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Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.fw001

The Foundations of Physical

Organic Chemistry: Fifty Years of
the James Flack Norris Award

In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.fw001

In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 ACS SYMPOSIUM SERIES 1209

The Foundations of Physical

Organic Chemistry: Fifty Years of
the James Flack Norris Award
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.fw001

E. Thomas Strom, Editor

University of Texas at Arlington
Arlington, Texas

Vera V. Mainz, Editor

University of Illinois at Urbana-Champaign
Urbana, Illinois

Sponsored by the
ACS Division of the History of Chemistry

American Chemical Society, Washington, DC

Distributed in print by Oxford University Press

In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 Library of Congress Cataloging-in-Publication Data

Names: Strom, E. Thomas, editor. | Mainz, Vera V., editor. | American

Chemical Society. Division of the History of Chemistry.
Title: The foundations of physical organic chemistry : fifty years of the
James Flack Norris Award / E. Thomas Strom, editor, University of Texas at
Arlington, Arlington, Texas, Vera V. Mainz, editor, University of Illinois
at Urbana-Champaign, Urbana, Illinois ; sponsored by the ACS Division of
the History of Chemistry.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.fw001

Description: Washington, DC : American Chemical Society, [2015] | [Oxford] :

Distributed in print by Oxford University Press | Includes bibliographical
references and index.
Identifiers: LCCN 2015041510 (print) | LCCN 2015046593 (ebook) | ISBN
9780841230712 | ISBN 9780841230729 ()
Subjects: LCSH: James Flack Norris Award in Physical Organic Chemistry. |
Chemistry, Organic--United States--History. | Chemistry, Organic--Awards.
| Chemistry--United States--History. | Chemistry--Awards.
Classification: LCC QD248.5.U6 F68 2015 (print) | LCC QD248.5.U6 (ebook) |
DDC 547/.13--dc23
LC record available at http://lccn.loc.gov/2015041510

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In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 Foreword
The ACS Symposium Series was first published in 1974 to provide a
mechanism for publishing symposia quickly in book form. The purpose of
the series is to publish timely, comprehensive books developed from the ACS
sponsored symposia based on current scientific research. Occasionally, books are
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.fw001

developed from symposia sponsored by other organizations when the topic is of

keen interest to the chemistry audience.

Before agreeing to publish a book, the proposed table of contents is reviewed

for appropriate and comprehensive coverage and for interest to the audience. Some
papers may be excluded to better focus the book; others may be added to provide
comprehensiveness. When appropriate, overview or introductory chapters are
added. Drafts of chapters are peer-reviewed prior to final acceptance or rejection,
and manuscripts are prepared in camera-ready format.

As a rule, only original research papers and original review papers are
included in the volumes. Verbatim reproductions of previous published papers
are not accepted.

ACS Books Department

In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 Preface
The symposium on which this book is based came about because one of
us (Tom Strom) became increasingly concerned about the status of his chosen
discipline, physical organic chemistry. With the recent flowering of organic
synthesis, physical organic chemistry seemed to be shrinking or perhaps it was
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.pr001

just being absorbed into the tool kit of the synthetic chemist. The only Nobel
Prize that can be reasonably attributed to a physical organic chemist is the 1994
award to George Olah, although Jeffrey I. Seeman has recently made a strong
case that R. B. Woodward was actually a physical organic chemist in disguise (1).
However, it is clear that Woodward’s 1965 Nobel Prize was awarded because of
his prowess in synthetic chemistry.
Tom decided to arrange a symposium for the ACS History Division that
examined the history and fundamentals of physical organic chemistry. He asked
his friend Jeffrey Seeman to be co-organizer. In examining themes for such
a symposium, Seeman noted that 2014 would see the awarding of the 50th
James Flack Norris Award in Physical Organic Chemistry. It became clear that
the research carried out by the winners of this award, sponsored by the ACS
Northeastern Section, gave insight into the fundamentals of the discipline. Jeff
and Tom decided on a two stage symposium: presentations by early winners of
the award and a panel discussion by recent award winners on the topic, “Whither
Physical Organic Chemistry.” The symposium then came together rather quickly
and was scheduled for the March, 2014, ACS National Meeting in Dallas, TX.
James Flack Norris was an early physical organic chemist, before the
discipline received its name. His picture is on the cover of this book, and
Arthur Greenberg led off the symposium with a talk on Norris. Then came talks
from Norris Award winners Ned Arnett, Ronald Breslow, Andrew Streitwieser,
John Brauman, Paul Schleyer, Kendall Houk, and Michael Wasielewski. The
participants for the closing panel discussion were John Baldwin, Ned Porter,
Matthew Platz, Hans Reich, John Roberts, and Michael Wasielewski.
ACS Books was very interested in issuing a volume on this historical
symposium. Co-organizer Jeff Seeman was unable to continue as a co-editor
because of the press of other activities. Tom asked his long-time friend and
chemical historian Vera Mainz to co-edit the volume, and she graciously agreed
to do so. Greenberg, Arnett, Breslow, Streitwieser, and Schleyer agreed to submit
book chapters, but Brauman, Houk, and Wasielewski were unable to do so.
However, Norris Award winners Ken Wiberg, Keith Ingold, and Wes Borden,
who were unable to participate in the original symposium, agreed to submit
chapters on their work.

ix
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 The steady progress toward completion of this volume ended abruptly with
the death of Paul Schleyer in November, 2014. In his last message to us on Nov.
19, he said he would try to finish his chapter the very next week. He died just two
days later. Paul was 84 years old, but he was still strongly involved in quantum
chemistry research and had a great deal left to give to chemistry and also to the
history of chemistry. Your editors were faced with the problem of transforming
his oral presentation, which we had on tape, into a written chapter. Also, we felt
that this volume should not only contain a chapter by Paul, but a chapter about
Paul. Eventually we were able to persuade Andy Streitwieser to provide such a
chapter. Fortunately, Andy was able to obtain Paul’s unfinished memoir, which he
had started but never completed for Jeff Seeman’s series of books by renowned
organic chemists. We thank Paul’s widow Inge for permission to use this material.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.pr001

Consequently, Paul Schleyer is represented in two chapters in this volume.

With the precedent of having a chapter about a deceased Norris Award winner
in the volume, we asked ACS Books for permission to have two more chapters
about deceased winners. This permission was given. Therefore, the book was
completed with a chapter on William Doering written by Ron Magid and Maitland
Jones and a chapter on Glen A. Russell written by Kathleen Trahanovsky and E.
Thomas Strom.
Our first words of thanks must go to the authors of our book chapters. We
are grateful for the sharing of their recollections and research with the readers of
this book. For financial support of the original symposium, we want to thank
the ACS History of Chemistry Division, ACS President Tom Barton, and the
Northeastern ACS Section. The ACS Division of Organic Chemistry was also
a sponsor of the original symposium. We also thank the HIST Program Chair
Seth Rasmussen for his assistance in arranging the symposium. We appreciate the
important work done by Jeff Seeman in obtaining the original group of speakers.
We thank the many reviewers of these chapters for their comments and corrections.
For their invaluable assistance in completing this volume, we thank Tim Marney,
Bob Hauserman, Arlene Furman, Lindsey Watson, and Tara Urban of ACS Books.
Someday someone will write a history of physical organic chemistry. This
volume, with its contributions by so many noted physical organic chemists, will
be an invaluable starting point for such a history.

x
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 References
1. Seeman, J. I. R. B. Woodward, A Great Physical Organic Chemist. J. Phys.
Org. Chem. 2014, 27, 708–721.

E. Thomas Strom
Department of Chemistry and Biochemistry
University of Texas at Arlington
Box 19065
Arlington, TX 76019-0065
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.pr001

Vera V. Mainz
Department of Chemistry
University of Illinois at Urbana-Champaign
600 S. Mathews Avenue
Urbana, IL 61802

xi
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 Editors’ Biographies
E. Thomas Strom
Dr. E. Thomas (Tom) Strom is an Adjunct Professor at the University of Texas
at Arlington (UTA), where he teaches organic and polymer chemistry. He came to
UTA after retiring from Mobil in Dallas, where he worked 32 years as a research
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ot001

chemist studying oil field chemistry. He was Chair of the ACS Division of the
History of Chemistry in 2011-2012. His research interests are in the history of
chemistry and the study of anion radicals by electron spin resonance spectroscopy.
He was one of the initial ACS Fellows and is a past winner of the Dallas-Fort
Worth ACS Section’s Doherty Award. He received his B.S.Chem degree from the
University of Iowa, his M.S.Chem degree in nuclear chemistry from UC-Berkeley,
and his Ph.D. in physical organic chemistry from Iowa State University working
under mentor Glen A. Russell. Previously he has co-edited two volumes in the
ACS Symposium Series: "100+ Years of Plastics. Leo Baekeland and Beyond"
(2011) and "Pioneers of Quantum Chemistry" (2013).

Vera V. Mainz
Dr. Vera Mainz is retired Director of the NMR Lab in the School of Chemical
Sciences at the University of Illinois at Urbana-Champaign. She received a B.S.
in Chemistry and Mathematics at Kansas Newman College (1976), a Ph.D. in
Inorganic Chemistry at the University of California Berkeley (1981, with R. A.
Andersen), spent 1-1/2 years working at Rohm and Haas in Springhouse, PA,
and had a postdoctoral position at the University of Illinois at Urbana-Champaign
(1983-1985) before becoming Director of the NMR Lab. She was elected to the
position of Secretary-Treasurer of the History of Chemistry Division (HIST) of
the ACS in 1995, and has served as Secretary-Treasurer since that time. Her
interest in the HIST Division was kindled when she presented her work on the
chemical genealogy of the University of Illinois (UI) Chemistry Department at
a HIST symposium on chemical genealogies in 1994. She has continued her
work in this area, posting her information to a website at http://www.scs.uiuc.edu/
~mainzv/Web_Genealogy/, and plans to update this project when her schedule
allows. Vera’s interest in the history of chemistry led her and her husband, Gregory
Girolami, to co-curate two exhibits at the Univ. of Illinois’ Rare Book Room:
1) From Alchemy to Chemistry: Five Hundred Years of Rare and Interesting
Books, http://www.scs.uiuc.edu/~mainzv/exhibit/; 2) Crystallography – Defining
the Shape of Our Modern World, found online at URL http://www.scs.illinois.edu/
xray_exhibit/. Vera was a member of the ACS Fellows Class of 2012, which

© 2015 American Chemical Society

In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 honored her contributions to the ACS (HIST and local section service) and the
many students she has helped while working in the NMR Lab.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ot001

306
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 Chapter 1

James Flack Norris: His Early Contributions

to Physical Organic Chemistry
Arthur Greenberg*
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch001

Department of Chemistry, University of New Hampshire, Durham,

New Hampshire 03824
*E-mail: [email protected]

In honor of the fiftieth anniversary of the James Flack Norris

Award in Physical Organic Chemistry, a brief biographical
sketch of Norris is presented along with discussion of his
research accomplishments in the contexts of the influence of
his doctoral mentor Dr. Ira Remsen and the early development
of physical organic chemistry. Dr. Norris had two distinct
academic careers, researcher and teacher at Massachusetts
Institute of Technology (MIT) and administrator and teacher
at Simmons College. A third career, scientific leader and
statesman, co-existed with these dual careers. This chapter
will briefly describe Norris’s researches in molecular addition
compounds, the triphenylmethyl system, Friedel-Crafts
chemistry as well as his twenty paper series on “The reactivity
of atoms and groups in organic compounds” (from 1920 through
1940).

The Early Days of Physical Organic Chemistry and Some

Modern Perspectives
The origins of the field recognized as “physical organic chemistry” may be
dated close to the start of the twentieth century. In 1895 Paul Walden demonstrated
(1) the stereochemical inversion that now bears his name. The concept of
steric hindrance had been introduced by Victor Meyer (2) one year earlier. In
1899, Julius Stieglitz made a solid proposal for the existence of carbocations
(3). In 1900 Moses Gomberg published his ground-breaking discovery of the
triphenylmethyl free radical (4). Explicit recognition of the field dates to the

© 2015 American Chemical Society

In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 period between 1920 and 1940 (5). Christopher K. Ingold published “Principles
of an Electronic Theory of Organic Reactions” in Chemical Reviews in 1934 (6)
and this was later expanded into his classic textbook, Structure and Mechanism in
Organic Chemistry, published in 1953 (7). Louis P. Hammett formally anointed
the field with his publication of the 1940 textbook Physical Organic Chemistry
(8). Consistent with this early history, the American Chemical Society (ACS)
presented the first James Flack Norris Award in Physical Organic Chemistry to
Christopher Ingold in 1965 and the second award to Louis Hammett in 1966 (see
the Appendix).
Hammett’s Preface is brief and essentially defines physical organic chemistry
as “…the investigation of the phenomena of organic chemistry by quantitative
and mathematical methods (8).” The title of Ingold’s book explicitly describes its
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch001

theme and, whereas Hammett’s 1940 textbook emphasizes kinetics and equilibria,
the first 196 pages of Ingold’s large tome emphasizes structural properties and
includes resonance theory and Hückel molecular orbital theory (7). The late
1950s and early 1960s witnessed the widespread and fundamental introduction of
physical organic chemistry into the undergraduate chemistry curriculum. Many
from my own generation were first explicitly introduced to physical organic
chemistry through Edwin S. Gould’s Mechanism and Structure in Organic
Chemistry (9) (note the permutation of Ingold’s title). Other excellent text books,
varying slightly in emphasis, soon followed (10–13).
The 1950s, 1960s and 1970s might well be considered to be a heyday of
“classical” physical organic chemistry with the great non-classical carbonium
ion controversy as its centerpiece. The sometimes thunderous arguments and
disagreements during this period, among some of the most distinguished chemists
of the era, led to refinements in the interpretation of substituent effects, solvent
effects, steric effects and anchimeric assistance. Ultimately, the controversy
was settled through spectroscopy experiments at temperatures approaching 0
K, coupled with increasingly reliable computational chemistry. During this
period other “shoots” began to emerge including the beginnings of mechanistic
biochemistry and nanotechnology. Indeed, even as its methodologies became
widely employed in many fields of investigation, practitioners started to worry
over whether physical organic chemistry, as a field, was still recognizable and even
“viable” (read fundable) as such. This author recalls attending an evening talk
in 1976 by a distinguished long-time physical organic chemist who pronounced
chemistry “a dead field” and confidently laid out his new strategy which was
to do only “useful” chemistry. Queried at the end of the talk about the totally
counter-intuitive results derived from the emerging field of gas-phase organic
ion chemistry (e.g. toluene a stronger acid in the gas phase than methanol), he
described this and similar such observations as “artifacts.” Still, the evolution of
chemical science and changes in funding priorities and criteria have led to (useful)
periods of self-doubt and self-examination. Such concerns provided impetus for
an International Union of Pure and Applied Chemistry (IUPAC) Symposium in
print concerning the past, present and future of physical organic chemistry (14).
Reports of the demise of physical organic chemistry remain premature. This is
readily appreciated by simply viewing the sheer scope of the table of contents of
the 1100-page, folio-sized 2006 tome by Eric Anslyn and Dennis Dougherty (15).

2
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 Early in the twenty-first century we find ourselves in a funding environment
increasingly demanding practical solutions to the problems of the day such as
“sustainability”, a term so widely and indiscriminately used as to become almost
as meaningless as it is highly fundable. Yet who would be so bold (or reckless) to
assert that they can predict the future outcomes of fundamental research in physical
organic chemistry? It was in 1959, that Richard Feynman first drew attention
to the concept of nanoscience (16). A year later Edel Wasserman reported the
first synthetic catenanes (17) and Gottfried Schill published Catenanes, Rotaxanes
and Knots in 1971 (18). Who could have envisioned that a generation later such
chemical exotica would play an important role in the design of nanodevices (19)?
Similarly, Robert Bergman provided strong experimental and theoretical evidence
for the esoteric, indeed evanescent, 1,4-benzyne (20). Some nineteen years later,
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch001

naturally-occurring anti-cancer agents including calicheamicin were discovered.

An enzyme “pulls a trigger” in this molecule, forming a 1,4-benzyne derivative that
attacks DNA in the cancer cell (21). Thus, while the principles and methodologies
of physical organic chemistry are widely adopted by many diverse scientific fields,
physical organic chemistry itself remains vital, recognizable and will undoubtedly
produce breakthroughs hard to anticipate today.
So where does the research of James Flack Norris fit into the development of
physical organic chemistry? He was, in fact, “present at the creation”, as Tidwell
(22) references Norris’s early preparation of carbocation salts (23). Norris’s
fundamental research was published even as he inveighed against tricoordinate
carbon (24) and Gomberg’s free radical. Moreover, his quantitative studies
during the 1920s and 1930s of the dependence of rates of reaction on substituents
and solvents certainly fit the Hammett definition of physical organic chemistry.
In the remainder of this chapter we will briefly explore biographical details of
Professor Norris’s life, the influence of his research mentor Professor Ira Remsen,
his contributions to the nascent field of physical organic chemistry, and the two
different James Norris Flack awards: the chemical education award, presented by
the Northeastern Section of the American Chemical Society (NESACS), starting
in 1951, and the award in physical organic chemistry presented by the American
Chemical Society at the national level starting in 1965.

Brief Biography of James Flack Norris

James Flack Norris (Figure 1) can be said to have had two nearly-distinct
academic careers. Superimposed upon these was another career as a chemistry
leader and scientist-statesman. His academic career started and finished at
Massachusetts Institute of Technology (MIT) during which his synthetic and
quantitative studies, very much congruent with Hammett’s definition, added
substantially to a burgeoning new field. This influence was recognized explicitly
by the James Flack Norris Award in Physical Organic Chemistry celebrated in
the present symposium. Norris spent a twelve-year hiatus period forming the
chemistry program at Simmons College, with one year on sabbatical at Karlsruhe.
This experience, complemented by important textbooks he authored, combined
3
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 with his teaching accomplishments at MIT and Simmons provided impetus
for the earlier endowed award, the James Flack Norris Award for Outstanding
Achievement in Teaching of Chemistry.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch001

Figure 1. Dr. James Flack Norris, Professor of Chemistry at MIT. (Courtesy

Department of Chemistry, MIT)

4
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 A number of sources provide details of the life and career of Professor James
Flack Norris (25–30), the most extensive being the 1951 piece by Blake (26),
reprinted in the special commemorative issue of The NUCLEUS in 1965 (27).
While the 1974 National Academy of Sciences Biographical Memoir compiled
and reformatted material from the earlier Tenney L. Davis article (25), its author
John D. Roberts also contributed insights about the significance of Norris’s
research (28).
James Flack Norris was born in Baltimore, Maryland on January 20, 1871.
He was the fifth of nine children born to Methodist Reverend Richard Norris
(1835-1897) and Sarah Amanda (Baker) Norris (1849-1917). Young Norris
graduated from Central High School in Washington, D.C. and attended Johns
Hopkins University and received his A.B. degree in chemistry, coming under the
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch001

influence of Professor Ira Remsen with whom he would complete his Ph.D. in
1895. His research involved study of “molecular addition compounds” including
those formed between amines and molecular halogens His interest in the analytical
chemistries of selenium and tellurium also developed during this period. Norris
was appointed Instructor at MIT in 1895 and promoted to Assistant Professor
in 1900 where he served until 1904. During 1904 Norris served as Chairman
of the Northeastern Section of the ACS. Clearly, his leadership qualities were
recognized early by his peers. On February 4, 1902 Norris married Anne Bent
Chamberlin (1876-1948). She was a student at the Museum of Fine Arts in
Boston and later became a pioneer in social work for the deaf. In 1903 Norris
was honored with a lectureship at Simmons College in Boston and in 1904 was
appointed the first Professor of Chemistry at Simmons. Simmons College was
established in 1899 with the aspiration of becoming the “MIT for women.” Norris
would spend his next twelve years at Simmons organizing its course of chemistry
instruction as well as the laboratories. From 1907 through 1910 he served as
Director of the School of Science. Sensing the need to apply physical chemistry to
his interests in organic chemistry, Norris spent part of the 1910-1911 period with
Fritz Haber in Karlsruhe. (The irony in this association would become apparent
almost a decade later following the end of World War I). Returning to Simmons,
he was appointed Chairman of the Department of General Science. Norris was
granted lectureships at Harvard during 1912 and 1913 where one of his students
was Louis P. Hammett (26). He remained at Simmons until 1915, then spent one
year as professor at Vanderbilt University before returning to MIT as professor
in 1916. Upon leaving Vanderbilt he was presented a silver cigarette case with
the inscription “Sunny Jim” (31), an apt nickname for this dapper, well-liked man
and one that would remain with him for the rest of his life.
In 1906, James and Anne Norris built a summer house on Long Lake
in Western Maine that they christened “Good Cheer.” It was in this relaxing
environment that Norris wrote the four books and subsequent editions that would
eventually seed the Norris Fund after Anne Norris’s passing. The first of these,
titled The Principles of Organic Chemistry, was published in 1912. The second,
Experimental Organic Chemistry, was published in 1915. By the time third
editions of these books appeared in 1933, each had sold a total, in all editions, of
over 70,000 copies (26).

5
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ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 In October, 1917 MIT granted Norris a leave of absence to work for the U.S.
Government on gas-related problems at the Bureau of Mines in Washington, D.C.
He was subsequently placed in charge of “Offence Chemical Research” at the
Bureau. In early 1918 he was commissioned a Lieutenant Colonel in the Chemical
Warfare Service, based in London. After World War I (1919), Norris was placed
in charge of investigating the German manufacture of poison gas including the
frequency of illness and death among workers at Bayer Company and Höchst (32).
It is not apparent from my brief perusal whether Norris had interviewed Haber in
1919. Haber’s tragic contribution to the war effort, supervising the employment
of 6000 steel cylinders filled with 160 tons of chlorine gas at Ypres in 1915, and
his researches and applications of poison gas, are well known (32). A patriotic
German, to the consternation of many, Haber was awarded the Nobel Prize in
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Chemistry in 1918 for his discovery of the fixation of atmospheric nitrogen to

manufacture fertilizers that ultimately saved millions from starvation. Born Jewish
he converted to Christianity. This did not mollify the Nazis and when they came to
power in 1933, he lost his positions in Germany, fled to England and died in 1934.
In 1919 Norris was honorably discharged, returned to MIT and resumed a
research career that focused initially on the Friedel-Crafts reaction. James Mason
Crafts was on the MIT faculty from 1870 through 1874, spent the next seventeen
years in Paris working with Charles Friedel, returning in 1892 as Professor. Crafts
was President of MIT from 1897 to 1900 and continued his research for over a
decade afterward. Thus, Norris had early access to Crafts as a faculty colleague as
well as during Craft’s later years in Boston. During the 1920s, Norris’s research
moved into areas easily recognized almost a century later as physical organic
chemistry. These studies involved the effects of substituents and solvents upon
reaction rates determined quantitatively and they will be very briefly outlined
below.
In 1924, James Flack Norris was appointed Chair of the National Research
Council Section on Chemistry and Technology. He was the last ACS President
elected to serve multiple terms (1925, 1926; ten previous ACS presidents had
served multiple terms consecutively or non-consecutively). On December 29,
1925, Norris gave the opening talk at the inaugural National Organic Chemistry
Symposium (33). Titled “The Opportunities for Research in Organic Chemistry”,
Norris had originally planned a talk titled “Quantitative Measurement of Organic
Reactivity of Organic Compounds (33).” This latter topic was, in all likelihood,
the basis of his subsequent guest presentation, “Chemical Reactivity,” delivered
at Columbia University during summer, 1926 (34). During the period 1925-1928
Norris was Vice President of IUPAC. He had been elected an Honorary Member of
the Royal Institution of Great Britain in 1925 and was a member of an educational
delegation to the USSR in 1928. In 1937 Norris received the Gold Medal of
the American Institute of Chemists honoring is accomplishments as “teacher and
investigator.” He served as Chairman of the Faculty of MIT during 1937-1939.
James Flack Norris was elected to membership in various august groups including
the American Academy of Arts and Sciences (serving as Vice President during
1936), the National Academy of Sciences (elected 1934), and as a fellow of the
American Association for the Advancement of Science (Chairman, Chemistry
Section in 1930). But it is almost irresistible to mention his membership in the

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In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
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 rather lesser known “Ouroboros.” This club, founded in 1916 (35), evolved from
the “Chemistry Round Table,” convened by members of NESACS in 1910. The
ouroboros is a mythical alchemical legged serpent that regenerates itself even as
it consumes its own tail. The membership of Ouroboros would include Theodore
Richards, Charles James, James Conant, Arthur Noyes, Louis Fieser and Kenneth
Wiberg among many luminaries. The first female member, Anna J. Harrison,
Professor at Mount Holyoke, was admitted to Ouroboros in 1970, eight years
before she became the first female President of ACS. Ouroboros seems to have
become extinct during the first decade of the twenty-first century (35).
Over the course of a four-decade-long academic career, James Flack
Norris authored roughly seventy publications (28) and mentored twenty-one
Master degree students (including three women) and thirty-eight Ph.D. students
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(including three women) (27). It must be noted here that as a junior faculty
member at MIT and during his period at Simmons, Norris had no graduate
assistants. The first two Norris-trained graduates received masters (S.M.) degrees
in 1920 and 1921 and his first Ph.D. student graduated in 1922 (27). One of his
masters students, Charles J. Pederson (S.M. 1927) would spend his subsequent
career at Du Pont and share the 1987 Nobel Prize in Chemistry with Donald
J. Cram and Jean-Marie Lehn. The title page of the 1937 Ph.D. thesis of 1965
Nobel Laureate Robert Burns Woodward is signed by Norris as Chairman of
the Department Committee of Graduate Students (36). Woodward famously
completed his B.S. (1936) and Ph.D. (1937) degrees at MIT in a total of four
years. Norris is revealingly quoted in the Boston Globe in 1937:

…we saw we had a person who possessed a very unusual mind and we
wanted it to function at its best. If the red tape necessary for less brilliant
minds had to be cut, we let it go. We did for Woodward what we have
done for no other person like him in our department. We think he will
make a name for himself in the scientific world (37).

In his brief dissertation acknowledgement Woodward thanked “…Professors

James F. Norris and Avery A. Morton, who have taken a particular interest in this
work…” (36). Norris was also Morton’s research mentor at MIT (Ph.D. 1924)
prior to the latter’s appointment to the MIT faculty.
During summer, 1940 successful cataract surgery in Norris’s right eye (June)
was followed by phlebitis in July and hospitalization for blood transfusions some
two weeks later. He died on August 4, 1940 survived by his wife Anne. The
devoted couple had no children. Anne Bent (Chamberlin) Norris (born May 29,
1879) (38) passed away on May 29, 1948. She had been elected in 1933 the first
female President of the American Society for the Hard of Hearing and continued
to serve this and other related organizations for many years to come. In her will
Mrs. Norris provided the Northeast Section of the ACS with a gift of $10,000,
also sharing the remainder of the estate equally with MIT. The will stated:

It is my wish that the Directors of said Society shall use the money in any
way they may see fit to perpetuate the memory of my said husband James
F. Norris.

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 This fund would soon form the basis of the Norris award in teaching and over
a decade later the Norris award in physical organic chemistry. These will be
discussed later.

The Influence of Ira Remsen upon the Career of James Flack

Norris
Although it might at first appear to be a routine academic exercise, the
influence of Norris’s Ph.D. advisor Ira Remsen (39) on his future career as
scientist, scientific leader and statesman was quite profound and worth examining
briefly. He left his mark on the education of American Ph.D. chemists from the
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late nineteenth century into modern times. Remsen saw no sharp dividing line
between inorganic and organic chemistries and made noteworthy contributions in
both fields (he lectured and authored important textbooks in both areas). Remsen
explored structure-reactivity relationships in organic chemistry during the final
quarter of the nineteenth century.
Ira Remsen (1846-1927) was born in New York City, received his
undergraduate education at the Free Academy (now the City College of New
York) and, obeying his father’s wishes, obtained his M.D. degree in 1867 at
the College of Physicians and Surgeons of Columbia University. However,
Remsen developed an interest in chemistry and, exercising his free will, travelled
to Munich hoping to work with Justus Liebig. Liebig was no longer taking
students so young Remsen worked with Privatdocent Jacob Volhard, learning
techniques in analytical chemistry. During this period, Friedrich Wöhler was an
occasional visitor to the Munich laboratory and in fall 1868 he inspired Remsen
to move to Göttingen. There Remsen pursued organic chemistry research under
the direction of Rudolf Fittig, receiving his Ph.D. in 1870. The twenty-four
year old Remsen followed Fittig to Tübingen where “he drank in the spirit of
the German laboratories” (39). Returning to the United States in 1872 with a
faculty appointment at the liberal arts institution Williams College, Remsen was
severely disappointed by the lack of interest and support for teaching experimental
chemistry (39). He did complete his masterful textbook Theoretical Chemistry,
an extraordinarily useful work that made the principles and breakthroughs of the
period widely accessible.
Despite the serious limitations at Williams, Remsen conducted experimental
research including studies of the oxidation of carbon monoxide and reactions of
phosphorus compounds. The concept of valence was still quite new and many
chemists held the view that each element exhibits a single valence. Thus, reaction
of PCl3 with chlorine yields what was commonly regarded as the “molecular
addition compound” PCl3.Cl2. Remsen, aware of Wurtz’s recent determination
of vapor density consistent with the formula PCl5, concluded that the reaction
of PCl3 and chlorine did in fact produce pentavalent phosphorus. Similarly, his
studies of the reaction of ozone with PCl3 led Remsen to interpret the product as
containing pentavalent phosphorus: O=PCl3 (39).
Ira Remsen was one of a galaxy of stars recruited to Johns Hopkins University
in 1876 (39). There he established a Ph.D. program based upon the German
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 model and revolutionized graduate education in chemistry in the United States.
At Hopkins much of his research focused on organic chemistry. An early interest
in structural organic chemistry led to “Remsen’s Law”- e.g. a methyl group ortho
to a sulfamido group (SO2NH2) is protected from certain oxidation reactions.
Remsen’s researches into what one might term “primordial physical organic
chemistry” is exemplified by an 1884 paper in which he demonstrated that
isopropyl bromide is less stable than n-propyl bromide in zinc and an acid but
more stable in alcoholic sodium hydroxide (39). Remsen’s student Norris would
eventually make such structure-activity comparisons quantitative (“physical
organic”) rather than simply qualitative. In 1879 Remsen and Russian chemist
Constantin Fahlberg, working in Remsen’s laboratory, published the discovery
of saccharin (39). Fahlberg would file patents in 1884 and 1886 claiming sole
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credit for the discovery and starting a business manufacturing and selling the first
commercial synthetic sweetener.
Ira Remsen was a scientific and academic leader and scientific statesman,
a path traversed by James Flack Norris decades later. Shortly after arriving at
Johns Hopkins, Remsen inaugurated The American Chemical Journal. After
publication of fifty volumes, Remsen agreed to incorporate it with The Journal
of the American Chemical Society (JACS). Remsen was elected President of the
American Chemical Society for 1902. He served as Acting President of Johns
Hopkins (1889-90) and President from 1901 through 1913. In 1909 Ira Remsen
was appointed by President Theodore Roosevelt to Chair a Board studying
administration of the pure food law (39). Based upon this very brief biographical
outline, it is reasonable to conclude that Ira Remsen exerted major influence upon
James Flack Norris in both scientific and public venues.

Early Scientific Research on Selenium, Tellurium and

Molecular Addition Compounds
The research of James Flack Norris under the mentorship of Ira Remsen at
Johns Hopkins University included the chemistry, notably analytical chemistry,
of selenium and tellurium. The earliest paper with Norris’s name on it was
co-authored with Remsen (40). Starting with a salt assigned the formula
SeBr4.SeOBr2.2(CH3)3N.HBr, reaction with bromine formed (CH3)3N.Br2. The
same product was obtained through reaction of trimethylamine with bromine.
Similar chemistry was observed between trimethylamine and iodine. Such
“molecular addition compounds” were poorly understood at the time. The
physical methods for testing their nature were quite limited- formation of unique
crystals upon reactions of molecular substances, new melting points, and percent
composition of constituent elements were among relatively few experimental
criteria. Theories about the bonding in these complexes included notions of
“residual affinities” of atoms in the molecules.
Henry Fay would co-author Norris’s next paper, which involved
determination of selenious and selenic acids (41). These two young chemists
first met as assistants at MIT. Three additional papers, also co-authored with Fay,
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 would follow between 1898 and 1900 (28). In 1902, Fay was best man at Norris’s
wedding.
Although first investigated at MIT, a decade after Norris finished his doctoral
studies at Johns Hopkins, it is worthwhile mentioning Norris’s continued interest
in selenium and tellurium. Among significant problems in the late nineteenth
and very early twentieth century were the “anomalies” in the ordering in the
periodic table of some elements according to atomic weight. One example
involves tellurium, heavier than iodine, rather than lighter than iodine as would
be expected by their placement:
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One simple explanation could be very minor contamination of tellurium samples

with another, heavier chemical element. However, in 1906 Norris confirmed the
purity and atomic weight of tellurium (42), so the apparent anomaly remained.
Today, we understand that this “reversal” is due to the presence of heavy isotopes
of tellurium (128Te; 130Te) in significant (each >30%) abundance. However, it was
only in 1907 that Bertram Boltwood characterized “ionium”, soon to be recognized
as an isotope of thorium (the term coined by Frederick Soddy in 1913). Also in
1907, Joseph John (“J.J.”) Thomson discovered canal rays associated with neon
corresponding to atomic masses 20 and 22. These measurements were confirmed
by Francis William Aston in 1919 using his early mass spectrograph.

Debating Tricoordinate Carbon with Moses Gomberg

Although the term “free radical” is in common (chemical) usage, the word
“radical” is understood by most non-chemists as referring to “extreme” conditions
(as in radical surgery) or in an “extreme” political context. However “radical”
can be defined as “of or from the root” or “foundation or source of something.”
In the late eighteenth century, Louis Bernard Guyton de Morveau introduced the
term “radical”, later adopted by Antoine Laurent Lavoisier, to describe RX + Y →
RY + X. Here radical R is exchanged between X and Y. How R moved from X to
Y was not imaginable. However, nineteenth-century chemists, especially organic
chemists, did pose such questions and tried to obtain or at least infer the presence of
the “free radical” (e.g. R). By the 1860s, the tetravalent nature of carbon was well
accepted. During the latter part of the nineteenth century a number of excellent
chemists claimed to have isolated free radicals but were quickly proven incorrect.
In 1900 Moses Gomberg reported his attempt to synthesize hexaphenylethane
through reaction of triphenylmethyl chloride with zinc metal (Wurtz reaction) in a
non-polar solvent free of oxygen (4). Zinc chloride precipitated leaving a yellow
solution. This solution reacted instantly with added iodine to form triphenylmethyl
iodide. The yellow solution also reacted instantly, when exposed to air, to form a
peroxide:
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In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
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 The observation of the stable triphenylmethyl free radical was indeed a radical
claim but was well accepted within a few years. At the end of his paper Gomberg
famously placed this injunction:

This work will be continued and I wish to reserve the field for myself.

At this time, Norris was investigating the Friedel-Crafts reaction and the possibility
of employing carbon tetrachloride and benzene to synthesize tetraphenylmethane.
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The reaction yielded triphenylmethyl chloride and therein did Norris collide with
Gomberg (23) who had just reported the compound even as the Norris manuscript
was ready for submission. Responding to Gomberg’s expansive territorial claim,
Norris countered (23):

He wishes to reserve this field for further work. As we have been working
with triphenylchloromethane in this laboratory for about a year, with a
view of preparing tetraphenylmethane from it, it seems advisable to give
a preliminary account of the work that has been accomplished, and to
describe briefly what is now in progress.

When Norris combined triphenylmethyl chloride, benzene and aluminum

trichloride in carbon disulfide solution, he failed to obtain tetraphenylmethane
but found instead a solid that was insoluble in the non-polar solvents benzene,
carbon disulfide, carbon tetrachloride and petroleum ether. The solid was
soluble in nitrobenzene but decomposed in alcohol, ether, acetone, chloroform
and acetic acid. The solid was reported as an addition compound of formula:
Al2Cl6.2(C6H5)3C.Cl (43) [later modified to (C6H5)3CCl.AlCl3)]. Norris realized
that under typical Friedel-Crafts reaction conditions, after addition of the third
benzene ring, a significant solubility change would occur resulting in precipitation
and no further reaction. The Friedel-Crafts conditions employed by Norris were,
of course, very different from the reaction conditions employed by Gomberg.
Indeed, as intimated by Tidwell (22), Norris was in fact exploring the chemistry
of the stable triphenylmethyl carbocation. Norris then reported reactions of
triphenylmethyl chloride and benzene in the presence of sodium metal (23).
This was, of course, uncomfortably close to Gomberg territory. In studying
the chemistry of triphenylmethyl chloride in concentrated sulfuric acid, HCl
was given off and the final product was triphenylcarbinol (24). Ironically, this
paper (24) was titled by Norris “On the Non-Existence of Trivalent Carbon.”
He concluded that the highly-unsaturated hydrocarbon prepared by Gomberg
was best represented as (C6H5)3C : C6H4 and implied that the structure included
the central carbon attached to two carbons on one of the benzene rings (24).
Gomberg, however, sharply criticized Norris’s studies on Wurtz-type chemistry
and made a convincing case that experimental divergences from his own results
were largely the result of incomplete purification by Norris of solvents (43).
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 Gomberg was totally unconvinced by the hydrocarbon formula advanced by
Norris. Indeed, he was irritated by Norris’s very presence in the field (43):

It seems, therefore, strange that Norris should at this stage give up

his original problem, the synthesis of tetraphenylmethane, and take up
the study of the action of metals upon triphenylchlormethane. I have
published only a preliminary paper upon this subject, asking that the
field might be reserved for myself.

Gomberg and Norris did agree on the experimental conversion of triphenylmethyl

chloride to the alcohol in concentrated sulfuric acid (43). While Norris lost
the triphenylmethyl radical debate to Gomberg, it is clear that he was an early
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contributor to stable carbocation chemistry. During the first decade of the

twentieth century, conductivity studies in high dielectric constant solvents would
demonstrate the reality of stable carbocation salts including triphenylmethyl
carbocation.

Contributions to Quantitative Organic Chemistry (1920s and

1930s)

In 1904 James Flack Norris left MIT to establish the chemistry program
at Simmons College. He would return to MIT in 1916, with war assignments
occupying his attention from 1917 through 1919. As a consequence, Norris
published one research paper (42) in 1906 and one each in 1907, 1910 and 1916.
Not until 1920 did Norris research papers reappear (three in the Journal of the
American Chemical Society) (27). One series of papers (1907, 1916 and 1920)
dealt with reactions of alcohols in aqueous solutions of HCl and HBr. Primary
alcohols were found to be very unreactive whereas benzyl alcohol and allyl
alcohol were highly reactive. The theme of exploring organic reactivities through
kinetics became the major thrust of his research program at MIT starting in 1916
(34). This is one area in which Norris departed markedly from his doctoral mentor
since Remsen was judged to be somewhat indifferent to physical chemistry
(44). In his 1926 presentation at Columbia University (34), Norris nicely laid
out his rationale for quantitative studies of organic reactions. In describing the
understanding at that time of the chemical reactions of inorganic substances,
Norris declared (34):

The modern conception of the changes involved in inorganic chemical

reactions are based on the quantitative study of the energy changes of
these reactions.

and further (34):

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 The facts summed up in Faraday’s law and in the electromotive series of
the elements made possible the broadest generalizations in regard to the
chemical behavior of the elements and their compounds.

In other words, the reactions of inorganic substances were, in Norris’s view,

determined by thermodynamics. While the situation in organic chemistry was
deemed far more complex (34):

Organic chemistry lacks such broad generalizations. The radicals in

these compounds correspond to the elements in inorganic chemistry. Can
these radicals be studied in some way to give results of a general nature
that are applicable in this field of interpretations of reactions, as is the
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electromotive series of the elements in inorganic chemistry?

When Norris resumed full-time faculty duties at MIT he entered a new

landscape in which chemical theories of reactivity of organic molecules were
being tested by experiment (5). Notably Arthur Lapworth had introduced a theory
of “alternative polarities” as early as 1905. Robert Robinson became friendly
with Lapworth in Manchester in 1909 and interested in the applications of
Lapworth’s theory. Combining Lapworth’s views and Johannes Thiele’s concept
of “residual valencies”, Robinson began developing a coherent theory of reactions
of unsaturated molecules including substituted benzenes. In 1925, Robinson
modified Thiele’s 1899 representation of benzene to provide the structure we
now commonly employ. Whereas residual valencies at the ends of 1,3-butadiene
explained the reactivity of this molecule (as well as its 1,4-addition chemistry), in
benzene, the ends meet in a cycle, neutralizing residual valencies and accounting
for its stability. Robinson also introduced the “curvy arrow” to illustrate the
movement of chemical bonds. He was an early supporter for applying electrons
(Lewis pairs) toward understanding mechanisms, a position advocated by Thomas
Martin Lowry (5).
An opposing school of thought grew in the early twenties around a theory of
“affinity demand” proposed by Bernard Flürscheim, related to work by Thiele and
Arthur Michael (5). Modifications, emphasizing electrical charges on atoms, were
introduced by Daniel Vorländer. This view deemphasized the need for electron
pairs. Christopher Ingold was, in fact, more in accord with this viewpoint.
The early differences in chemical theory between Robinson and Ingold
intensified in 1923 and 1924 and reached a head in 1926 when Robinson came
close to accusing Ingold of plagiarism. However, from 1926 onward, Ingold
proceeded to define the developing field of mechanistic organic chemistry,
introducing, for example, the terms “nucleophile” and “electrophile.” The
chemistry historian William H. Brock terms Ingold “…the great systematizer of
twentieth-century organic chemistry who firmly established the importance of
physical chemistry in understanding the subject” (45). Robinson’s efforts would
henceforth be increasingly directed to the studies of structure and synthesis of
natural products that would eventually earn for him the 1947 Nobel Prize in
Chemistry. Still, he made one large last effort in publishing in 1932 a pamphlet
detailing his interpretation of organic reaction theory (46). However, this

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 work was quickly overshadowed by Ingold’s extensive 1934 review article
(6). In 1930 one of the greatest partnerships in twentieth century chemistry
began when Edward David Hughes was appointed by Ingold (initially) as a
post-doctoral fellow at University College in London. Hughes was a master of
experimental kinetics and, with Ingold, soon combined kinetics, stereochemistry
and mechanism and developed the nomenclature of nucleophilic substitution. The
Robinson-Ingold rivalry would continue for decades. As Brock notes (47): “For
although the documentary evidence is lacking, Ingold and Hughes had seriously
believed in the 1930s that Robinson, as Britain’s most senior and respected
chemist, lay behind the opposition that their views provoked.”
A 1920 paper, co-authored with Dorothy M. Tibbetts (48), was built upon
two earlier research areas: molecular addition compounds and the triphenylmethyl
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system. In this paper, the authors included a succinct statement characterizing the
early philosophy of physical organic chemistry:

…especially in the field of organic chemistry…the chemist has it in his

power to change by the use of the proper substituents the nature of the
molecule and thus develop or reduce its ability to form addition products
with other substances.

Triphenylmethyl chloride was said by Norris to have an “active chlorine”

which is readily hydrolyzed and its high “residual affinity” or “latent affinity”
(i.e. high latent energy) is also manifested in its ability to form molecular
addition compounds such as (C6H5)3CCl.AlCl3. In contrast the “firmly-bound”
chlorine in methyl chloride does not form molecular addition compounds.
Diphenylmethyl chloride does not form analogous addition compounds although
p-phenyldiphenylmethyl chloride does form a molecular addition compound (48).
No mention was made in this paper of carbocation salts.
In 1925, the first of a series of twenty papers titled “The Reactivity of Atoms
and Groups in Organic Compounds” was co-authored with Avery A. Ashdown
and appeared in the Journal of the American Chemical Society (49). In it Norris
explored the relationship between reactivity and structure. In reactions between
p-nitrobenzoyl chloride and eleven alcohols, second-order rate constants varied by
a factor of almost seventy [relative values for RO-H: R = CH3, 100; R = CH3CH2,
45.7; R = (CH3)2CH, 5.4; R = (CH3)3C, 1.46].
In his presentation at Columbia University in summer, 1926 (34), Norris
summarized his on-going research on the reactivities of alcohols, alkyl chlorides
and acyl chlorides. In this presentation Norris emphasized the critical importance
of the quantitative measurement of chemical reactivities. In describing the
dependence of rates of reaction of derivatives of C6H5COCl with ethanol, he
reported data for o-, m- and p-substituted compounds. Table 1 includes a small
selection of data from this paper (acid chloride reactions were run at 0 °C and
alkyl chloride reactions at 25 °C).

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 Table 1. Rates (relative to unsubstituted, X = H) of ethanolysis for a series of
substituted benzoyl chlorides and diphenylmethyl chlorides selected from
Table 1 in reference (34).
Substituent (X) C6H5COCl derivatives (C6H5)2CHCl derivatives
H 1 (assigned) 1 (assigned)
m-Cl 3.17 0.0451
p-Cl 1.74 0.421
p-CH3 0.567 18.76
p-CH3O 0.79 3200
p-NO2 17.7 -------
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In describing the inverse influences of these substituents on the rates of these

two sets of reactions, Norris did not postulate an underlying explanation. At the
time he considered the differentiation of acyl halides from alkyl halides, based
upon the typically far greater reactivities of the former group, to be “an entirely
arbitrary one” since suitable substitution could produce alkyl halides more reactive
than acyl halides. Although different mechanisms were undoubtedly suspected,
there was no discussion of mechanism nor was there specific discussion of the
enormous rate enhancement noted for the p-methoxy substituent in Table 1. It is
likely that thirty-two year old Louis P. Hammett, appointed to the Columbia faculty
three years earlier, was present at this lecture and participated in discussions with
Norris. Two years earlier, J.N. Brønsted had published the first example of a linear
free energy relationship (50):

This refers to the dependency of reaction rate (k) on ionization constant (Ka) in
general acid-catalyzed reactions. Hammett would publish his famous linear free-
energy relationship some thirteen years later (51):

This relationship refers to the dependence of equilibrium (K) or rate (k) constants
on the electronic nature of a substituent on a benzene ring (σ) and the sensitivity of
a reaction type to electronic effects (ρ). This work would eventually systematize
the types of kinetic findings published by Norris.

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 The twentieth and final paper in the series “Reactivity of Atoms and Groups
in Organic Compounds was co-authored with Arthur E. Bearse, and published
in 1940 (52). This paper was received in January, 1940. Hammett’s famous
textbook was published later that year. Although Norris’s paper considers both the
acidities of substituted benzoic acids and their rates of conversion to the chlorides
with SOCl2, there is no reference to Hammett’s earlier work. Three other papers
authored by Norris, all focusing on Friedel-Crafts chemistry, were submitted and
published in JACS early in 1940. Later that summer Norris died.
In his biographical sketch of James Flack Norris (28), John D. Roberts
provided the follow summary of Norris’s scientific career:

Norris was rather less successful in his work on reactivity than was
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his younger counterpart at Harvard, James B. Conant, who displayed

an almost unerring instinct for choosing reactions for study of greater
simplicity and involving wider ranges of reactivity, along with an
excellent feel for the basic physical chemistry involved. Nonetheless,
Norris had the prescience to be at the forefront of the still-developing
area of making comparisons of organic reactivity under controlled
conditions, and some of the reactions he was first to study are among the
most important in preparative chemistry.

The James Flack Norris Awards

Anne Chamberlin Norris died in 1948, and her will provided a sizeable
endowment, to be administered by the Northeastern Section of the American
Chemical Society, to honor the memory of her late husband (53). A committee was
established to decide how best to use the bequest. The decision was announced
in January, 1950 to establish the James Flack Norris Award for Outstanding
Achievement in Teaching of Chemistry. The first awardee (1951) was George
Shannon Forbe, Professor Emeritus, Harvard University. Following retirement,
Dr. Forbe was a lecturer at Northeastern University in Boston. Initially, awards
were presented in alternate years (1951, 1953 and 1955), then one in 1956, spring
and fall awards in 1957 and 1959 and a single annual award starting in 1960.
The initiative that led to the James Flack Norris Award in Physical Organic
Chemistry came from Henry A. Hill, who was Chairman of NESACS in 1963
(54). Hill, a graduate of Johnson C. Smith University in Charlotte, North Carolina,
would later become the first African American President of ACS (1977). He
obtained his Ph.D. at MIT in 1942 and had overlapped briefly with Professor
Norris. Hill learned that the Norris Fund had “…grown both in book value and
income, and is now in excess of the fondest expectations of ten years ago” (54).
An ad hoc committee was formed that included Avery A. Ashdown, a Norris
Ph.D. graduate, and four other MIT alumni, met in February 1963. The decision
was made to fund a physical organic chemistry award that would be administered
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In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 by the American Chemical Society. The committee also authorized funding to
assist in the furnishing of a James Flack Norris room in the new MIT chemistry
building (54). The national ACS accepted responsibility in June of that year and
the first award was presented to Christopher K. Ingold in 1965 (see the Appendix).
A Symposium on Physical Organic Chemistry, to celebrate the first award, was
held on September 14, 1965 at the National ACS Meeting in Atlantic City,
New Jersey. Joseph F. Bunnett (Brown University) chaired the meeting. Other
speakers in addition to the honoree, Christopher K. Ingold (University College,
London), were Robert B. Woodward (Harvard University), Andrew Streitwieser,
Jr. (University of California at Berkeley), C. Gardner Swain (Massachusetts
Institute of Technology), Charles A. Bunton (University of California at Santa
Barbara), Maurice M. Kreevoy (University of Minnesota), and Frederic P. Olsen
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(University of California at Riverside). Happily and most fittingly, Professor

Emeritus Streitwieser made a presentation at the March 17, 2014 symposium
celebrating the fiftieth anniversary of the award.
In 1972 ACS granted $10,000 to Simmons College to furnish a James
Flack Norris room. It served as collegial interaction space for faculty, staff and
students until 2000 when the building was totally renovated (55). A photograph
of Dr. Norris hangs proudly in the Department of Chemistry and Physics main
office. Indeed, a chemistry major was a member of the first graduating class of
Simmons College (55). It is also worthwhile to mention the James Flack Norris
and Theodore William Richards Undergraduate Summer Scholarships awarded
by NESACS. Richards, a professor at Harvard, was the first American to win the
Nobel Prize in Chemistry (1914).
There are some interesting and noteworthy points in revisiting the James Flack
Award in Physical Organic Chemistry. Two awardees also received the Norris
Award in Teaching: Louis P. Hammett (1960) and Paul D. Bartlett (1978). There
is a single case in which parent (Christopher K. Ingold in 1965) and offspring
(Keith U. Ingold in 1993) each received this award. None of the awardees were
or subsequently became Nobel laureates. This explicitly raises a question my
own Ph.D. advisor Pierre Laszlo rhetorically posed to me in the 1960s: Why had
no Nobel Prize in Chemistry been yet awarded to a physical organic chemist?
Far be it from me to plunge into the treacherous waters of controversy in which
this question has often bobbed through the years. It is likewise interesting that
Nobel laureates who have made important contributions to physical organic
chemistry, such as Donald J. Cram (1987) and George A. Olah (1994), were not
Norris awardees. Olah, in particular, discovered conditions for making transient
carbocation intermediates relatively long-lived and observable by NMR. And
for that matter, what about Robert Burns Woodward? In a paper titled “R.B.
Woodward, A Great Physical Organic Chemist” (56), Jeffrey Seeman reminds
readers of the 1965 Nobelist’s impact well beyond organic synthesis. Here
one also sees some parallels (and differences) between Woodward and Robert
Robinson, who similarly received his Nobel Prize for work in synthetic organic
chemistry but certainly left an early mark upon physical organic chemistry. In his
paper (56), Seeman also notes that in April, 1957 B.S. Hutchinson, the Chairman
of NESACS, informed Woodward that “…the committee has unanimously chosen
you as the nominee” (i.e. for the James Flack Norris Award for Outstanding

17
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 Achievement in the Teaching of Chemistry). Seeman could locate no record of
Woodward’s response. Thus, for reasons not readily discernable, R.B. Woodward,
received neither of the two Norris awards despite being a very strong case for
the physical organic award and actually having been chosen unanimously for the
teaching award.
Today physical organic chemistry remains recognizable as such even as it
forms the foundation for research in very diverse fields. These contributions
continue to be recognized by the James Flack Norris Award in Physical Organic
Chemistry in areas diverse enough that predictions of the future (14) will almost
certainly miss surprises that are unimaginable at the present time.
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Dedication

In memory of Dr. Paul von Ragué Schleyer (February 27, 1930 – November
21, 2014).

Acknowledgments
The author is grateful to Thomas Strom who extended the invitation to make
a presentation at the symposium in Dallas on March 17, 2014. For initiating my
interest in physical organic chemistry, I wish to acknowledge my Ph.D. advisor
Pierre Laszlo and three professors, each a physical organic Norris awardee, from
whom I took classes in the 1960s: Kurt Mislow, Paul von Ragué Schleyer and
Peter Stang. I was also very fortunate during this formative period to have been
stimulated in seminars by Kenneth Wiberg, Michael Dewar and Ronald Breslow,
all physical organic Norris awardees. I am grateful to Joel Liebman, Richard
Johnson, Glen Miller and Gary Weisman who have been long time friends,
colleagues, teachers and sounding boards. I also wish to express my gratitude
to Jeffrey Seeman who provided me with ideas, critiques and early access to
interesting archival materials. Special thanks to Susan J. Greenberg who helped
me to organize the March 17, 2014 presentation.

Appendix
Winners of the James Flack Norris Award in Physical Organic Chemistry
[For the list of winners of the James Flack Norris Award for College Chemistry
Teaching visit the Northeast Section of the American Chemical Society (NESACS)
site: www.nesacs.org/awards_norris.html]

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Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch001

References
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Dtsch. Chem. Ges. 1896, 29, 133–138.
2. Meyer, V. Über ein seltsames gesetz bei der esterbildung aromatischer säuren.
Ber. Dtsch. Chem. Ges. 1894, 27, 510–512.
3. Stieglitz, J. On the constitution of the salts of imido ethers and other
carbamide derivatives. Am. Chem. J. 1899, 21, 101–111.
4. Gomberg, M. An instance of trivalent carbon: triphenylmethyl. J. Am. Chem.
Soc. 1900, 22, 757–771.
5. Brock, W. H. The Norton History of Chemistry; W.W. Norton & Co.: New
York, NY, 1993; pp 506−569.
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Rev. 1934, 34, 225–274.
7. Ingold, C. K. Structure and Mechanism in Organic Chemistry; Cornell
University Press: Ithaca, NY, 1953.
8. Hammett, L. P. Physical Organic Chemistry; McGraw-Hill Book Co., Ltd.:
New York, NY, 1940; p v.
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and Winston, Inc.: New York, NY, 1959.
10. Hine, J. Physical Organic Chemistry; McGraw-Hill Book Co., Inc.: New
York, NY, 1962.
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 11. Leffler, J. E.; Grunwald, E. Rates and Equilibria of Organic Reactions; John
Wiley and Sons, Inc.: New York, NY, 1963.
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NY, 1964.
13. Kosower, E. M. An Introduction to Physical Organic Chemistry; John Wiley
& Sons: New York, NY, 1968.
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for the 21st Century: A Symposium in Print. Pure Appl. Chem. 1997, 69 (2).
15. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry;
University Science Books: Sausolito, CA, 2006.
16. Feynman, R. P. There’s Plenty of Room at the Bottom. Presented at American
Physical Society Meeting, Pasadena, CA, December 29, 1959.
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17. Wasserman, E. The preparation of interlocking rings: a catenane. J. Am.

Chem. Soc. 1960, 82, 4433–4434.
18. Schill, G. Catenanes, Rotaxanes and Knots; Academic Press: New York, NY,
1971.
19. Stoddart, J. F. Putting mechanically interlocked molecules (MIMs) to work
in tomorrow’s world. Angew. Chem., Int. Ed. 2014, 53, 11102–11104.
20. Jones, R. R.; Bergman, R. G. p-Benzyne. Generation as an intermediate in a
thermal isomerization reaction and trapping evidence for the 1,4-benzenediyl
structure. J. Am. Chem. Soc. 1972, 94, 660–661.
21. Nicolaou, K. C.; Dai, W.-M. Chemistry and biology of the enediyne
anticancer antibiotics. Angew. Chem., Int. Ed. 1991, 30, 1387–1416.
22. Tidwell, T. T. The first century of physical organic chemistry: a prologue.
Pure Appl. Chem. 1997, 69, 211–213.
23. Norris, J. F.; Sanders, W. W. On triphenylchlormethane. Am. Chem. J. 1901,
25, 54–62.
24. Norris, J. F. On the nonexistence of trivalent carbon. Am. Chem. J. 1901, 25,
117–122.
25. Davis, T. L. James Flack Norris. Ind. Eng. Chem. 1936, 14, 325–326.
26. Blake, J. T. The first James Flack Norris Award for Excellence in the Teaching
of Chemistry (reprinted from the NUCLEUS, June, 1951). The NUCLEUS
1965, 42, 307–309.
27. Special Issue Commemorating the First Presentation of the James Norris
Flack Award in Physical Organic Chemistry. The NUCLEUS, Newsletter of
the Northeastern Section of the American Chemical Society; August, 1965;
Vol. 42, No. 10.
28. Roberts, J. D. James Flack Norris 1871-1940. Biographical Memoir;
National Academy of Sciences: Washington, DC, 1974; pp 413−426.
29. Onofrio, J. James Flack Norris. Maryland Biographical Dictionary;
Somerset Publishers, Inc.: 1999; pp 401−402.
30. Simon, M. S. The James Flack Norris Award for Outstanding Achievement
in the Teaching of Chemistry. The NUCLEUS 2002, 81 (3), 4.
31. Wikipedia (accessed October 6, 2014) seems as good a source as any for
researching “Sunny Jim.” He is the dapper, jaunty fellow depicted on the front
of Force Toasted Whole Wheat Flakes. Force cereal was originally produced
in the U.S. in 1902, discontinued here in 1983 but is apparently still available

20
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 in the United Kingdom. Its bit of advertising doggerel (just in case you were
curious):
Jim Dumps was a most unfriendly man,
Who lived his life on the hermit plan;
In his gloomy way he’d gone through life,
And made the most of woe and strife,
Till Force one day was served to him.
Since then they’ve called him “Sunny Jim.”
32. Fitzgerald, G. J. Chemical warfare and medical response during World War
I. Am. J. Public Health 2008, 98, 611–625.
33. Fenlon, E. E.; Myers, B. J. Profiles in chemistry: a historical perspective on
the National Organic Symposium. J. Org. Chem. 2013, 78, 5817–5831.
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34. Norris, J. F. Chemical Reactivity; Columbia University Press: New York,

NY, 1927.
35. Jones, P. R.; Atkinson, E. R. Ouroboros- A New England Chemists Club.
Presented at American Chemical Society Meeting, Boston, MA, August 19,
2002.
36. The author thanks Jeffrey Seeman for disclosing and providing this
information.
37. Moore, P. J. T.; Bowden, M. E. In Robert Burns Woodward- Architect
and Artist in the World of Molecules; Benfey, O. T., Morris, P. J. T., Eds.;
Chemical Heritage Foundation: Philadelphia, PA, 2001; pp 3−10.
38. Moore, M. C. Anne Chamberlin Norris. The NUCLEUS 1965, 42, 315–316.
39. Noyes, W. A.; Norris, J. F. Ira Remsen 1846-1927. Biographical Memoir;
National Academy of Sciences: Washington, DC, 1931; Vol. 14, pp
205−257.
40. Remsen, I.; Norris, J. F. The action of the halogens on the methylamines. Am.
Chem. J. 1896, 18, 90–95.
41. Norris, J. F.; Fay, H. Iodometric determination of selenious and selenic acids.
Am. Chem. J. 1896, 18, 703–706.
42. Norris, J. F. On the elementary nature and atomic weight of tellurium. J. Am.
Chem. Soc. 1906, 28, 1675–1684.
43. Gomberg, M. On trivalent carbon. Am. Chem. J. 1901, 25, 317–335.
44. Servos, J. W. Physical Chemistry from Ostwald to Pauling: The Making of
a Science in America; Princeton University Press: Princeton, NJ, 1990; pp
93−94.
45. Brock, W. H. The Norton History of Chemistry; W.W. Norton & Co.: New
York, NY, 1993; p 507.
46. Robinson, R. Outline of an Electrochemical (Electronic) Theory of the
Course of Organic Reactions; Institute of Chemistry: London, U.K., 1932.
47. Brock, W. H. The Norton History of Chemistry; W.W. Norton & Co.: New
York, NY, 1993; p 531.
48. Norris, J. F.; Tibbetts, D. M. Organic molecular compounds. J. Am. Chem.
Soc. 1920, 42, 2085–2092.
49. Norris, J. F.; Ashdown, A. A. The reactivity of atoms and groups in organic
compounds. I. the relative reactivities of the hydroxyl-hydrogen atoms in
certain alcohols. J. Am. Chem. Soc. 1925, 47, 837–846.

21
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 50. Brønsted, J. N.; Pedersen, K. J. Die katalytische zerzetzung des nitramids
und ihre physilalische-chemische bedeutung. Z. Phys. Chem. 1924, 108,
185–235.
51. Hammett, L. P. The effect of structure upon the reactions of organic
compounds. Benzene derivatives. J. Am. Chem. Soc. 1937, 59, 96–103.
52. Norris, J. F.; Bearse, A. E. The reactivity of atoms and groups in organic
compounds. XX. The effect of substituents on the relative reactivities of the
hydroxyl group in derivatives of benzoic acid. J. Am. Chem. Soc. 1940, 62,
953–956.
53. The Northeastern Section of the American Chemical Society (NESACS):
James Flack Norris Award. www.nescas.org/awards/_norris.html (accessed
October 18, 2014).
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54. Hill, H. A. The James Flack Norris Award in Physical Organic Chemistry.
The NUCLEUS 1965, 42, 305–30.
55. Personal communication from Dr. Rich Gurney, Chair, Department of
Chemistry and Physics, Simmons College, to A. Greenberg on February 17,
2014.
56. Seeman, J. I. R. B. Woodward, a great physical organic chemist. J. Phys.
Org. Chem. 2014, 29, 708–721.

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In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
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 Chapter 2

My Study of Optical Activity - From the Distant

Past to the Present with Stops in-Between
Kenneth B. Wiberg1,*
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Department of Chemistry, Yale University, New Haven, Connecticut 06520

1Present address: 865 Central Ave., Apt A404, Needham,

Massachusetts 02492
*E-mail: [email protected]

Physical organic studies encompass a variety of subjects. Our

work included studies of small ring compounds where the
higher energies lead to increased reactivity, studies of the
mechanisms of reactions including oxidations, the application
of ab initio theoretical calculations to studies of reactivity and
properties, as well as spectroscopic studies. More recent work
has concentrated on the relationship between structure and
conformations on specific rotations.

Introduction
In the late 1940’s when I was a graduate student at Columbia University
working with Bill Doering, I was given the problem of looking at the
stereochemistry of t-alkyl group migration in electron deficient molecular
rearrangements. It was known that s-alkyl groups migrated in a seemingly
concerted process, but t-alkyl was sufficiently different that it might involve bond
cleavage to a t-alkyl cation followed by recombination. Starting with a chiral
t-alkyl group this might lead to some loss of chirality. I proceeded to prepare
methylethylisobutylacetic acid and to resolve it via a salt with brucine (1). A
number of its reactions were studied and it appeared that chirality was normally
conserved.
In the course of this work I became interested in the connection (if any)
between structure and the sign and magnitude of the optical rotation. Not much
was known about the subject at that time, and so my interest lay mainly dormant

© 2015 American Chemical Society

In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 for the next 50 years, except for noting the development of the quadrant and
octant rules (2), and Brewster’s rules (3).
In the meantime, I carried out a number of studies that had a physical-organic
context and I wrote a book (4) on the subject while enjoying a sabbatical leave
(1962) in Rudolf Criegee’s Institute at Karlsruhe, Germany.

Small Ring Compounds

Some of our work dealt with the synthesis and properties of
small ring compounds such as the remarkably strained and reactive
hydrocarbons, bicyclo[1.1.0]butane (1) (5), [1.1.1]propellane (2) (6), and
Δ1,4-bicyclo[2.2.0]hexane (3) (7). They have calculated strain energies of 64, 98
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and 87 kcal/mol respectively (8). These values are large considering that the C-C
bond strength is 88 kcal/mol.

Despite its strain, 1 and its derivatives are readily formed via 1,3 elimination
reactions (5). The central bond is easily cleaved. The propellane, 2, also may
be formed via a 1,3-elimination reaction of the bridgehead dihalides via reaction
with t-butyllithium (6), and an elimination reaction from a tetrachloride provides
a convenient way in which to prepare it in some quantity (9). The structure is
interesting in that it has an "inverted" tetrahedral geometry at the bridgehead
carbons (10). It adds iodine to form the diiodide, and reducing agents readily
convert it back to 2. It is very reactive toward free radicals and can lead to
polymers (6). It’s thermal stability is probably related to the high energy of any
species formed by breaking a C-C bond. The alkene, 3, can be prepared in dilute
solutions, is a very reactive dienophile and these reactions lead to propellanes.
It readily dimerizes to form a pentacyclic propellane that opens to form an
interesting diene (7).
It was important to have experimental information about some of these
small ring compounds. This led us to determine the heats of formation of
cyclopropene, 1-methy-cyclopropene, methylenecyclopropane, bicyclobutane
and cyclobutene using a flame calorimeter (11). The heat of formation of the
"aromatic" cyclopropenyl cation could be derived from the heat of formation of
cyclopropene and the results of a mass spectrometric study (12). Our interest in
energies led us to make use of a precision solution calorimeter that we designed
to be completely computer controlled including data collection and analysis (13).
It was used to study steric interactions in the hydrolysis of orthoesters (14) and
lactones (15). It was also used in determining the heats of hydration of alkenes
(16), heats of reduction of ketones (17) as well as in a conformational study (18).
Solvolytic studies of exo and endo-5-bicyclo[2.1.0]pentyl tosylates
(4,5) gave a 106:1 relative reactivity (19) (much greater than that for the
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In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
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 corresponding norbornyl derivatives), and related studies of cis- and trans-fused
bicyclo[3.1.0]hexyl derivatives gave further information on the role of orbital
interactions on reactivity (20). The interest in these and related compounds led to
a study of what is now known as "molecular mechanics" and to develop the first
general computer program for strain energy minimization (21).
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Mechanisms of Oxidation
Other studies dealt with the mechanisms of oxidation of organic compounds
by hydrogen peroxide (22), potassium permanganate (23) and chromic acid
(24). The reactions we studied included the oxidation of aldehydes, alkenes
and alkanes. Both MnO4- and HCrO4- usually undergo an initial two electron
reduction in their reactions with organic compounds, commonly leading to a
Mn(5) or Cr(4) intermediate. Using a stopped flow reactor and UV detection, it
was possible to observe the formation and subsequent reaction of the inorganic
intermediates, and to observe their rates of reaction (25). The studies of oxidation
reactions led to an interest in deuterium kinetic isotope effects (26) and to writing
a review on the subject (27).

Computational Studies
We became interested in using ab initio theory to supplement our experimental
studies. A group equivalent scheme was developed to easily estimate heats of
formation from the calculated total energies (28). One problem in making use of
this theory results from the fact that the calculations are for the gas phase whereas
most reactions are carried out in solution. We studied the use of Onsager’s reaction
field model (29) and methods derived from it (30) to estimate solvent effects, and
applied it to several problems (31).
Chemists have often been interested in electron density distributions and
assigning charges to atoms in molecules. We applied Bader’s theory of atoms
in molecules (32) and electron density difference maps to the question of why
the energies of fluorinated methanes are linearly dependent with the number of
fluorines, whereas this is not true with other substituents (33). We found that each
fluorine in carbon tetrafluoride has the same electron distribution and charge as
the fluorine in methyl fluoride. Thus, the carbon charge increases linearly with
the number of fluorines resulting in increasing C+-F- Coulombic attraction (34).
We have reviewed the differences in the charge that result from using the several
available models (35), and we have examined the relationship between bond
dipoles and the intensities of IR bands (36).
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In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 As a result of a question from G. B. Ellison, we became interested in
substituent effects on X-H bond dissociation energies (BDE). In the case of
RO-H, experimental results showed that the BDE decreased from 119 in HOH to
105 in MeO-H and 87 kcal/mol in HOO-H (37). We found that it was possible
to accurately reproduce these and other experimental results computationally
using CBS-APNO (38). Structural effects, calculations of spin densities, and
studies of electron density distributions showed that the main effect was a two
center-three electron conjugative interaction that stabilized the radical center (39).
A subsequent more extended study included second row elements and found in
interesting difference between P and S in their ability to interact with a radical
center (40). The differences between compounds with C=O and C=S also were
examined (41).
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Spectroscopic Studies
NMR spectroscopy has become the most important structural tool for organic
chemists. It was known that hydrogen chemical shifts are normally upfield from a
hydrogen nucleus, whereas carbon chemical shifts are normally downfield from a
bare carbon nucleus (42). Thus, hydrogens experience a diamagnetic interaction
that depends on the electron density about it, whereas carbons experience mainly
a paramagnetic interaction that results from the coupling between the ground state
and the excited states of the molecule in the presence of a magnetic field. We have
examined the contribution of the excited states and the effect of their orientation
and thereby gained a better understanding of the carbon chemical shifts (43).
Ultraviolet spectroscopy provides information about some electronically
excited states of molecules. However, studies in solution lead to broadening of
vibrational structure in the UV bands. We have made use of vacuum ultraviolet
(VUV) spectroscopy for gas phase measurements including spectral regions
where atmospheric oxygen absorbs. Bicyclobutane is an example where the
vibrational structure of the bands could be observed, allowing the transitions to be
assigned (44). Calculations clarified its photochemical transformation leading to
butadiene and cyclobutene (45). Other studies made use of calculations to assist
in gaining an understanding of the experimental results (46).
Infrared spectroscopy provides information on the inner workings of
molecules. We have carried out extended studies of many molecules such
as cyclopropene (47), cyclohexane (36), bicyclo[.1.10]pentane (48) and
[1.1.1]propellane (49).

Back to Optical Activity

I "retired" in 1997 when I turned 70, and in that year Polavarapu published
the first ab initio optical rotation calculation (50). It made use of the 1928 report
by Rosenfeld (51) of his derivation for an equation for optical rotation based on
the newly developed wave mechanics:

26
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 where M is the molar mass in g/mol, v is the energy of the polarized light, νba is the
transition energy to exited state b, and Rba is the rotatory strength for the transition.
The rotatory strength, Rba is given by

and couples the ground state a to excited state b under the simultaneous action of
the electric (µE1) and magnetic (µM1) dipole transition operators. The summation is
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over all of the excited states of the molecule. Thus, the observed rotation depends
on accurately calculating both the electric and magnetic transition moments for a
given transition and taking the product of them for each excited state, followed by
a summation. This becomes a formidable computational effort, and could not be
done until there was both improvements in ab initio theory and the development
of fast computers.
The electric transition moment, such as for the π→π* transition of an alkene
lies along the bond coordinate, whereas a magnetic transition moment, such as for
an n→π* transition of a ketone goes about the axis. A product of the two would
describe a helix that can be either right or left handed. This in turn can lead to
an interaction with polarized light leading to either positive or negative sign of
rotation.

Rather than using Rosenfeld’s equation given above, Polavarapu (50) recast it
in a form in which one would not have to do a sum over excited states, and allowing
a more direct calculation. This was followed by a number of related studies. One
that caught my attention was by Stephens, Devlin, Cheeseman and Frisch (52) that
made use of density functional theory (DFT) and showed that reasonably accuracy
(±35°) could be achieved.
This reinvigorated my interest in optical activity, especially when the needed
code became available in a development version of the Gaussian program (53), I
returned to thinking about my old interest in the relationship between structure and
optical rotation. In the following "optical rotations" (OR) will be used as a short
hand for specific rotations that are defined as

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In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 where the cell length is given in dm (usually 1.0) and the concentration is given in
g/ml or as the density with neat liquids. It has the units of deg. dm-1(g/mL)-1 The
wavelength of the polarized light is given as λ.

Experimental Studies of Optical Activity

When the rotation for a compound is measured, one observes the weighted
average over its possible conformations. Here was a place where calculations
could provide information that could not be obtained by direct measurement,
and the calculated values could be compared against experiments by applying
the mole fractions of the conformers derived from the energy differences among
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

conformers using the Boltzmann equation. Since for many compounds, these
energies are not experimentally available, a calculation of the conformer energies
allows the rotations to be estimated, providing a double check on the accuracy of
the calculations.
In our first study, we examined one of the simplest of chiral compounds, 3-
choro-1-butene (54). This was prepared in chiral form and the specific rotations
were obtained in several solvents. This compound has three conformers resulting
from rotation about the CH2=CH-CH2 single bond (Figure 1). The relative energies
of the conformers were obtained from a scan of the energy as a function of torsion
angle (Fig 2), and the rotation also was calculated as a function of the torsion angle
(Figure 3) The relative free energies of the conformers were obtained using G2 (55)
allowing them to be estimated at 298K giving 1.05 and 1.10 kcal/mol for the two
gauche conformers. The calculated results are in good accord with experimental
meaurements of the conformer energies (56).
It was surprising to find the wild swings of the rotation with a range of -526 at
τ = 180′° to +435 at τ = 320° when the compound has a maximum rotation of only
[α]D = ±57.3°. Using the populations of the two conformers obtained from the G2
energy differences, and the calculated rotations shown in Figure 3, an estimated
rotation is on the order of -99.7 whereas the observed rotation was [α]D = -57.3.
Thus the rotation was estimated to be twice as large as observed. Since this was
one of the earliest studies of its type and led to remarkably large changes in OR, it
seemed important to obtain further information. It might be noted that a later study
by Tam, Abrams and Crawford (57) found that density functional theory was not
adequate for calculations for this compound, and that a coupled-cluster method
(CCSD) was able to give a much more satisfactory result.
In order to see if the double bond were responsible for the deviation between
calculated and observed rotations, we examined 2-substututed butanes where X =
F, Cl, CN and C=CH (58). These substituents are convenient in that they do not
add to the number of conformers. In addition they would be expected to lead to
significant differences in electronic levels that are involved in the calculation of
optical rotation, and this was confirmed by measurement of their VUV spectra. It
is well known that compounds such as these have three conformations, trans and
two gauche. The energies of the conformers were obtained by using G3.

28
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Figure 1. 3-Chloro-1-butene conformers

Figure 2. Calculated conformational energies

29
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Figure 3. Calculated Optical rotation profile for 3-chloro-2-butene

The OR of these compounds were calculated using B3LYP/aug-cc-pVDZ, and

the results are summarized in Figure 4. Despite the obvious differences among
the substituents there is remarkable similarity between the curves for the four
compounds. This suggests that in this case, substituents have a small effect other
than creating the chiral center. This was a surprising conclusion.
The observed specific rotation is the weighted average for the three
conformers. The averaged rotations were calculated using G3 (59) calculated
conformational energies allowing a comparison with the experimental rotations
(Table 1).
With these compounds there is fairly good agreement between experiment
and theory. Here, one must remember that the calculations refer to the gas phase
whereas the observed values are for the condensed phase. In some cases these
differences can become significant.
The agreement between observation and calculations could be fortuitous, and
it remained to be seen if the calculated rotations for the individual conformers of 2-
chlorobutane are in agreement with the calculated values. Some useful information
may be obtained from the temperature dependence of the optical rotation that
results from the effect of temperature on the conformer ratio. The conformational
energies have been studied experimentally giving an average value of ΔG ≈ 700
cal/mol. The data from the temperature dependence study should be given by

where αA is the rotation for the low energy conformer and α′ is the average of
that for the higher energy conformers. A least squares treatment gave a specific
rotations of -77.4° for the low energy conformer and 37.4° for the average of the
30
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 higher energy conformers. This may be compared with the calculated values of
-77.6° and 34.6°. The remarkably good agreement is probably in part fortuitous,
but the result confirm that the DFT-OR calculations for 2-chloro- butane are
quite good. A similar study for 2-cyanobutane (2-methylbutyronitrile) found
slightly poorer agreement with the calculated rotations about 25% larger than the
experimental values.
These results suggest that the calculations for saturated compounds may be
significantly more satisfactory than for their unsaturated analogs. This may be a
result of the double bond π→π* transition not being treated well using DFT.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Figure 4. Relationship between calculated optical rotations and the C2-C3

torsion angle

31
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 Table 1. Calculated and observed specific rotations at 589 nm for
conformational mixtures at 25° C.
X Calculated Observed,neat Observed,soln
F -17.2 na
Cl -37.1 -33.8 -33.8
CN -45.1 -36.3 -34.1
HCC -57.8 -46.8
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Twisted Achiral Compounds

The large conformational effects suggest that achiral compounds may give
significant optical rotations when twisted from planarity. This was examined
for a number of hydrocarbons including 1-butene and n-butane (Figure 5) (60),
and showed that these compounds can give large rotations in their twisted forms.
However, there is a significant effect of theoretical method on the observed values.

Figure 5. Calculated optical rotations for twisted butane.

32
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 The calculated optical rotation as a function of C-C torsion energy for butane
has a simple maximum at 90° with the 6-311++G** basis set, but it become much
different using the aug-cc basis sets. This is seen more dramatically in a study of
30° rotated ethane (i.e. halfway between staggered and eclipsed). Some calculated
rotations are given in Table 2.

Table 2. Effect of basis set on B3LYP calculated specific rotations at 589

nm for 30° rotated ethane.
Basis set bf [α]D
6-311++Gd 86 -495.1
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

6-311(2+,2+)Gdf 100 -505.1

6-311++(2d,2f) 114 -226.3
6-311++G(3df,3pd) 186 -19.5
cc-pVDZ 58 -208.4
cc-pVTZ 144 -215.3
aug-cc-pVDZ 100 +41.2
aug-cc-pVTZ 230 +53.6
aug-cc-pVQZ 436 +57.8
UGBSIP 766 +59.1

Most of the details concerning the basis functions used in the calculations
are not of importance in the present context. The column bf gives the number of
functions (s,p,d..) that were used in the calculation, and generally the larger the
number the better the result. The first 4 basis functions are of the "Pople" type
and they are very satisfactory for most purposes such as geometry optimizations
and vibrational frequency calculations, whereas the latter basis functions are of
the "Dunning" type that also are normally very satisfactory. But, as seen from
the calculated results, especially the change in sign, in the present case there is a
large difference with the Dunning functions giving the correct sign as shown by
the largest basis set calculations
These basis sets include extra functions beyond the basic group. It is possible
to improve on the simple s, p, d .. set by allowing these nucleus centered functions
to move in response to the electric fields in the molecule. This happens when
a small amount of a p-function is added to s, and when some d is added to p,
etc. In addition, it sometimes is useful to include "diffuse" functions that are
much larger than those in the basic group. They are indicated by + in the Pople
sets and by aug in the Dunning sets and are frequently needed in calculations
for anions (61). Hydrogens diffuse functions are rarely important for geometry
optimizations and so only diffuse s functions are included in the "Pople" sets but p

33
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 diffuse functions also are included to the "Dunning" sets. It is these latter functions
on hydrogens that lead to the large differences noted in Table 2. The addition of
p-diffuse functions to the former set corrects the problem.
Why should these seldom needed functions be so important for optical activity
calculations? A clue is given by the density difference plot in Figure 6 that shows
the difference resulting from the addition of these functions (60). At a relatively
far distance from the nucleus, there are some helical differences that result from
the directional nature of the diffuse p functions. Optical activity results from
the helical character of the wave function, and switching stereoisomers results in
switching the sense of helicity and the sign of rotation. This effect of helicity is
strikingly seen in the optical rotations of helicenes (6) (62) and triangulenes (7)
(spiro-linked cyclopropanes) (63) that give very large rotations.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Figure 6. Difference density plot between calculations with and without diffuse p
functions on hydrogens of twisted ethane.

34
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Use of Minimal Basis Sets

Calculations of optical rotation have come to using increasingly large basis
sets with many polarization functions and diffuse functions. The observations
given above made us think that much of this complexity might not be essential for
the calculations. Would it be possible to reproduce their results using a minimal
basis set (STO-3G or 3-21G) to represent the core and valence electrons and
then add a full set of diffuse functions (64)? Could a minimal basis set "steer"
the diffuse functions that are relatively far from the nuclei so that they adopt
the essential helical character of the molecule? In a non-resonant situation, the
polarized light used to interrogate the molecule might interact mainly with the
outer diffuse electron density leading to rotation of the plane of polarization.
This seemed something of a wild idea, but we decided to explore it. The study
was concerned with how well the large basis set B3LYP calculations could be
reproduced.
We used both STO-3G and 3-21G as the minimal basis sets and added
diffuse functions from the aug-cc-pVDZ and aug-cc-pVTZ basis set. The object
was to see if the results from B3LYP calculations using large basis sets could
be reproduced, A number of compounds were examined including α-pinene,
3-carene, norbornenone and 2,3-pentadiene (64). The results were quite good,
and an example from the carenes is shown in Figure 7.
Here the rotation increases as the number of basis functions is increased. They
reach an asymptote as shown by the horizontal lines and the points are numbered.
The first two points are for STO-3G and 3-21G that are very small basis sets, and
it is clear that they do not give satisfactory computational results. Point 5 is for
cc-pVDZ (no diffuse functions). Point 3 involves just the addition of diffuse s, p,
d functions to STO-3G and gives a calculated rotation that is essentially the same
as that derived from the use of a very large basis set . Even with large basis sets
such as for points 14(cc-pVTZ) and 20 (cc-pVQZ), diffuse functions are needed
giving points 19 and 21. The remaining points are identified in ref. (64).

35
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Figure 7. Effect of basis set on the calculated optical rotation of 3-carene at 355
nm (upper), 589 nm (center) and 633 nm (lower). The x axis gives the number of
basis functions on a logarithmic scale. The open symbols represent unaugmented
basis sets and the solid symbols are for the augmented sets.

Gas Phase Measurements

Until recently studies of optical rotation could not properly compare the
calculated values with the experimental results because they were obtained in the
condensed phase, either neat or in solution whereas the theoretical calculations
36
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 refer to the gas phase. Although a heroic effort by Biot (65) in 1817 to study
the optical rotation of turpentine in the gas phase showed that the vapor had a
rotation, the experiment ended rather disastrously when the vessel containing
the boiling turpentine broke open and was set on fire. There were some other
attempts to carry out gas phase studies but they were hampered by the low density
of molecules in the gas phase and the small rotations for most molecules.
This problem was solved by my colleague Prof. Patrick Vaccaro who made
use of a cavity ring-down cell that allow multiple passes through the cell (Figure
8) (66).
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Figure 8. Cavity ring-down polarimeter

Here, the sample is placed in an evacuated cell having high reflexance mirrors
at each end. A laser pulse is prepared and sent into the cell though one mirror. The
light that gets into the cell will be reflected by the other mirror, and at each pass,
some light will leak through the second mirror and will be analyzed. This provides
the opportunity to have the effect of a very long path length. But, this alone would
not lead to the observation of optical rotation since the effect of light moving in
the forward direct would be reversed in the back direction. This can be avoided
by inserting two quarter-wave plates, and the region between them will respond to
the optical rotation of the sample.
Chloropropionitrile is one of the simplest chiral compounds, and we have
examined the (S)-(-) form derived from (S)-(+)-alanine in some detail (67). It has a
rotation of [α]D = -14.5 as a neat liquid. A determination of the gas-phase rotation
gave [α]D = -8.3. It can be seen that there is a significant effect of phase. The OR
in solution was obtained in a number of solvents, giving a range of [α] from -11.6
in acetonitrile, to -17.4 in cyclohexane and -34.6 in benzene.
We have studied solvent effects on equilibria and reaction rates and found that
free energies in cyclohexane, di-n-butyl ether, acetone and acetonitrile usually
are linearly related to the Onsager dielectric constant function, (ε+1)/(ε+2) (29).
The function takes a zero value for the gas phase and goes to 0.5 for the highest
dielectric constant solvents. The correlation would be expected based on the
reaction field model of solvent effects (29). Extrapolation usually yields a value
close to that observed in the gas phase when this is available (31).
37
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 Application of this model to chloropropionitrile OR gave the result shown in
Fig 9. There is a linear correlation, but extrapolation to the gas phase led to a value
of -22, quite far from the observed value of -8.3. We have found that this is the
usual case for optical rotation. Chemists generally think of cyclohexane solutions
to be similar to the gas phase, but for optical rotation, acetone and acetonitrile
solutions usually give the closest OR to the gas phase.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Figure 9. Relationship between optical rotation and solvent dielectric constant

The effect of solvent on optical rotations has been studied computationally

at the DFT level by using a polarizable continuum model (PCM) (68). It was
unfortunately not able to give a very satisfactory result, but better results have
been obtained by using discrete solvent molecules in the calculations (69).
However, this involves averaging over solvent conformations, and the added
molecules greatly lengthen the execution times.

Sum-over States Calculations

It is clear that excited states are intimately connected with optical rotation. It
would be of interest to know which states are the most important. For example,
it is commonly thought that the carbonyl group is very important in the OR
of ketones (2). It is possible to obtain information on this subject from a
sum-over-states calculation of OR making direct use of the Rosenfeld equation.
Electronically excited states can be obtained by calculations using time dependent
38
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
 density functional theory (TDDFT) and this code in Gaussian also gives the
Rotatory strength for each transition. Thus, it is now relatively easy to carry out
the calculation. We have examined this for a number of molecules (70).
Chloropropionitrile gives a typical result. As with most molecules, the first
excited states are not the main source of the observed OR as may be seen in Fig 10.
The rotation continues to depend on the number of excited states beyond 100. It is
necessary to examine a very large number of states (Figure 11) in order to come to
a constant value for this quantity. It is fortunate that linear response methods have
been developed that do not need to deal with excited states directly.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Figure 10. Sum-over-States Study for Chloropropionitrile including the first

125 excited states.

Figure 11. Sum-over-States for Chloropropionitrile including >1500 excited

states.
39
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
Publication Date (Web): November 24, 2015 | doi: 10.1021/bk-2015-1209.ch002

Figure 12. Relationship between specific rotations for a norbornenone model

and its C=C-C-C torsion angle

Norbornenone
Of the compounds that we have examined, there is one, (S)-(-)-norbornenone
(6), that behaves differently. This compound was first prepared in chiral form by
Mislow and Berger (71). They found a specific rotation in isooctane solution of
[α]D = -1160 that is very large for such a small and relatively simple molecule.
The saturated derivative, norbonanone (7) has a rotation of ~20. A B3LYP/6-
311+G* calculation for 6 gave a rotation of -1260 (52) that was in remarkably
good agreement with the experiment. A sum-over-states study found that the first
electronic transition was largely responsible for the rotation (70). This is one of
the few molecules for which this is the case.

40
In The Foundations of Physical Organic Chemistry: Fifty Years of the James Flack Norris Award; Strom, et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2015.
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mindig, hogy a tutaj balszegletét a viz folyása ellen tartsa.
Holdvilággal minden elkészülhet. Hát kend, öreg, mit sirat még?
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– Jaj öreg, a szegény tótokat odafenn Árvában soha se viszi el az
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kiheverik, azért a magyar ember csak nem megy koldulni a
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nyolcz esztendeje már, hogy rajta van az árviz, nem is megy le róla
soha; azért még sem pityergek, hanem látok dolog után. Kiteremti
az Isten, kinek mire szüksége van; nem hal meg Magyarországon
éhen senki, csak a két tenyerét ne sajnálja.
Az öreg meggondolta a dolgot s azt mondta, hogy „biz igaz a!“
– No nem sirunk hát többet. Ezt se tesszük. Hanem ha szabad
megtudakolnunk becsületes nevét; mondaná meg, hadd hirdetnénk
az ismerőseinknek, ki szabaditott meg e mostani
szorongattatásunkból? hogy még az unokáinknak is meghagyhatnók,
kit emlegessenek meg, a midőn az uj házak mestergerendáin olvasni
fogják az „épitődött Anno Domini hányban? a nagy árviz után!“
Aladár és Ankerschmidt e kérdésnél már a csónakban ültek,
Aladár megnyomta utitársa lábát, hogy hallgasson, ő pedig
visszafordulva e nevet mondá.
– Az én nevem Weltumsegler Jonathan.
Az öreg megcsóválta a fejét s azt jegyzé meg:
 – No, ez sem igaz ám: tisztesség nem esik mondván.
Aladár pedig a vizbe nyomta a lapátot s a parton állók üdvriadala
mellett vágott neki ismét az özönnek.
– Ön a szerénységet egész a restelkedésig viszi, feddé az ifjut a
lovag ur; hogy még a nevét sem fedezé föl a jámborok előtt; a kik
valóban oly hálaérzettel kérték azt.
– Nem restelkedésből tettem én azt, hanem azért, mert a
jámborok szája eljár, s igy azután a nevemet majd nemcsak az
unokák emlegetnék, hanem a Bezirks-Vorstandok is.
– Ah! igen? ön attól tart, hogy a hatóság megtudná önnek e
dicséretes tettét, s fél tőle, hogy valami kitüntetést kap, s még a
hivatalos lapban nyilvánosan megdicsérik. Már igy értem.
– Dehogy érti. Attól tartok, hogy a mint lefut a viz, meglátják a
sok levágott fát a kamarális erdőben, megidéznek „wegen
Forstfrewel“ s ugy rám olvassák a paragraphust, hogy meg sem
moczczanhatok ellene, már pedig én, ki előkelő várfogoly voltam,
restelnék most megint alsóbb fokozatu fegyenczházi fogságba
kerülni.
Már ez ellen aztán Ankerschmidtnek sem volt semmi szava.
– Siessünk haza felé. Két órát eltöltöttünk itten, azt most
éjszakával kell helyrepótolnunk.
– Ön kifáradhatott.
– Még nem érzek belőle semmit.
– Szivesen felváltanám.
– Kardot, evezőt soha sem adok ki a kezemből. Különben most
már könnyebb munkánk lesz, a viz-folyás mentébe jutottunk.
– Nem látni még a falu tornyát?
 – Nem. De azért jól ismerem az utat. Sötét éjjel is oda találnék;
hát még fényes holdvilágnál.
A csónak csakugyan sebesebben haladt, mint délelőtt, most már
nem tiszta átlátszó vizen, alulról feltündöklő zöld vetés, pipacsvirág
fölött; hanem rút, szemetes habarékban, a mint az egyenesen jött a
Tiszáról, felszine ellepve nádgyökérrel és réti szénával.
Valami távol vadaskert lakóit felverhette a viz, azok ott usztak
végig a csónak előtt hosszu sorban, oly közel, hogy Aladárnak várni
kellett, mig a hosszu convoi elhalad előttük; a pompás szarvasok
ágbogas agancsai, az őzünők okos fejecskéi meg sem rebbentek
emberi közelléttől s a szarvascsorda közepén ott uszott nagy
lubiczkolással – egy csikasz farkas.
– Ha ezek a jegenyésre menekülnek: az én embereimnek lesz ma
vadpecsenyéjük, s két hét mulva bünvádi perük – vadórság miatt.
A nap jól lehaladt már, mire Aladár jelezte, hogy a falu tornya
látszik már a tenger látkörén.
Hanem még az nagy messzeség. A sikság optikája csalárd.
Aladár tanácsolá Ankerschmidtnek, hogy még ne nézegessen
hátra, mert beletelik három óra, a mig kastélyát megpillanthatja;
addig sokkal jobb lesz, ha végig fekszik a csónakban s megkisért
egyet aludni, a mire nagy szüksége lehet a tegnapi álmatlan éj után.
Ankerschmidt megfogadta, hogy lefeküdjék, azt ugyan erősen
állitá, hogy azért nem fog elaludni, minélfogva aztán, a mint a fejét
letette, csakugyan rögtön el is nyomta az álom.
S ha valaha fog valamiért köszönettel tartozni az életben
Garanvölgyi Aladárnak, ugy ez azon tanácsadása lesz, hogy aludja át
ezt az időt.
Azt az időt, a mi alatt a csónak a lakóhely felé közeledik.
 Hogy ne lássa perczről perczre közeledni azt a képet, mely a
fényes holdvilágnál oly kisértőn emelkedik ki a vizből; egy
összeomlott kastély képét.
Aladár látta ezt már, oly messziről, a minőre jó szemei elláttak,
hogy Ankerschmidt kastélyának teteje meggörbült: minden
evezőnyomás, mely közelebb hozta a tárgyat, világosabbá tette a
romlást, már a dült ablakok, a szétvált falak repedéseit lehete látni;
már a leomlott szárnyak, a beszakadt homlokzat romjai is kitüntek s
Aladár örült nagyon, hogy egyik evező nyomásról a másikra nem
látja ezt Ankerschmidt közelebb-közelebb jönni, ugy, miként ő.
Késő éjre járt az idő, az egész tájt nagy csend ülte: az a csend, a
mi az ébrenlevő lelkét megnépesiti bántalmas gondolatokkal; az
elhagyottság csendje.
Pusztitó elem foglalta el az egész sikot; a láthatáron két hold
látszott egymás felé közeliteni: egyik az égen, másik a vizen.
E szomoru világitásnál, mint nyomasztó álomlátás közeledett
egyre az Ankerschmidt kastély romalakja, minden evezőcsapásnál
jobban kitüntetve düledékeit. A félrecsuszott ablakok, a lefordult tető
felmeredő szarufái, a szétvált nyilás a tüzfalon, a magára maradt
kémény, egy egy meztelen boltozat, mindig világosabban rajzolódtak
az estderünél. Nemsokára az is kivehető lett, hogy a vizár a földszint
ablakain át hatolt be, s a mint a csónak végig haladt a homlokzat
előtt, a mint a kastély közepén be volt roskadva, azon keresztül,
mint egy perspectivben meglátszott az ősi alacsony kastély alakja, az
nem omlott össze.
Aladár kétszeres igyekezettel feszité a lapátot; s tekintetét le nem
vette az alvó utitársról. Az volt szándéka, hogy nem költi őt fel;
elevez szótlanul a rom mellett, ne lássa ő azt meg, s csak akkor
fogja őt felkölteni, midőn nagybátyja házához értek, ki bizonyosan
megfogadta a jókor küldött tanácsot. Ott aztán bizonyosat fognak
hallani a kastélyban voltak sorsa felől.
 De talán az álomra hunyt szemek is látnak valamit; s az álmodók
megérzik, ha közelit az a nagy gond, mely lelküket álmodva is eltölti,
s épen ugy látja most Ankerschmidt a csónakban végig fekve, azokat
a halomra dült köveket, azokat az összerecscsent gerendákat s a
házán keresztül omló hideg fekete árt, mintha nyitott szemmel
nézné; csakhogy ő még többet is lát, a kövek közt gyermekének
véres testét, s a fekete vizárban a mint annak szép hosszu selyem
haja végig-végig uszik. Az alvó homlokán nehéz veriték gyöngyözött
alá s szakgatott lélekzetében tehetlen kiáltások hangjai töredeztek.
Aladár aggodalmas sietséggel evezett el a dult kastély előtt; s
már már sikerült azt elhagynia, midőn az utczából, melynek végén a
kastély állt, egy másik csónak bukkant ki, melyet a kanyarodástól
eddig nem lehetett látni.
A holdvilágnál ép oly hamar ráismert Aladár a másik csónakosban
Kampósra, mint az ő reá, de mielőtt inthetett volna neki, hogy
maradjon veszteg, már késő volt; Kampós uram örömében akkorát
rikoltott, hogy arra minden alvónak fel kelle riadni.
– Hahó! ifja tensuram! Hahó! kiálta a lelkes ur, csáklyája végére
tüzve kalapját.
– Csitt, az Istenért ne kiabáljon… dörmögé Aladár, a házsorba
igyekezve jutni.
Már késő volt. Ankerschmidt az első kiáltásra felriadt fektéből, s a
mint szemeit felnyitotta; a legelső kép, a mit meglátott, összeomlott
kastélya volt. Talán ugyanazon látás, a miről folyton álmodott, testté
válva.
Nehány perczig mereven, jégszemekkel, halott arczczal nézett a
rémképre; azután felugrott, maga elé kapott, s az őrület hangján
kiálta fel: „leányom!“
Ha Aladár jókor meg nem ragadja, a vizbe esik.
„Leányom!!“ orditá magán kivül a hadastyán.
 – Ott van nálunk! nincsen semmi baja! lármázott Kampós uram,
ki most észrevevé, milyen rettenetes ostobaságot követett el, s
iparkodott minden tőle kitelhető tudományával Aladár
lélekvesztőjéhez csáklyázni, erősen szerencséltetve azt a felfordulás
minden esélyével.
Ankerschmidt arcza e szóra egyszerre kaczagásra vált, kaczagott,
mint egy gyermek, mint egy őrült.
– Igazán? Igaz-e az! Megszabaditották? semmi baj sincs? Mely
kérdések mindegyikét a naptár minden szenteire esküdve bizonyitá
Kampós uram; oly pazarul bánva az ugysegéljenekkel, mintha nagy
rablásért vallatnák.
– Nincsen semmi baj méltóságos uram. Ámbár elég orozva jött ez
a gonosz veszedelem, éjnek idején; még sem történt semmi
szerencsétlenség. A mint a harangot meghuzták, az öreg ur
egyszerre talpon volt; kijött hozzám, kérdezte mi baj? Én mondtam,
hogy a görgitői csőszök lóháton nyargalva jöttek, hogy már a
határban a viz. No hát akkor be kell tömetni az utolsó kaput. A mint
ez meg volt, már jött nagy harsogással az alsó utcza végén, épen a
méltóságos ur kastélya felől az Isten haragja, a házak az utczán
végig mind el voltak már töltésekkel rekesztve, hanem az utcza
egyszerre viz alatt állt s ma estig az ablakok aljáig emelkedett, de
azokon felül nem. A mi töltéseink ugy állják köröskörül, mint egy vár.
A mint a viz csónakázható lett, azt mondta az öreg ur: „no Kampós,
mit csinálnak most Ankerschmidték? azok nem fogadták meg az
intést.“
– Erről beszéljen; erről, sürgeté őt a lovag, kit épen csak leánya
érdekelt.
– Igen is. Tehát mondám, hogy azok bizonyosan usznak. No hát
akkor le kell ereszteni a csónakot. (Ugyan jó, hogy ezt a csónakot
előre küldte Aladár urfi!) Majd én magam kormányzok! monda az
öreg ur, s ekkor törte meg először fogadását, hogy nem megy ki a
házból, nyolcz esztendő óta. Magam, még egy evező legénynyel, egy
hosszu kötéllel, egy lábtóval megindulánk a kastély felé. Nagy volt
ám már akkor a hiba. Mondtam a nagyságos urnak, hogy a bécsi
pallér megérdemelné, hogy bezsindelyeznék a fejét. A mint a pincze
megtelt vizzel, egyszerre félre ment minden boltozat. S a falakon
akkora repedések támadtak, hogy keresztül lehetett rajtok látni. A
cselédnép jajveszékelve kiabált az ablakokban, s senki sem látott
utána, hogy valami módját keresse a menekülésnek. Mint később
megtudtuk, csak a kisasszonynak volt helyén a lelke, hogy egy nagy
zongora tokot lehozasson a padlásról; abból valami dereglyét
készitendő, de neki sem fogadott senki szót, hogy fölmenjen a
padlásra, mind attól félt, hogy a lépcső leomlik, s ő ott reked. Az
öreg ur látva a veszedelmet, neki támasztá a lábtót az erkélynek, s
maga felmászva rajta, belépett az ingadozó házba; s a sok rendetlen
futkosó cselédséget jól lehordva, megparancsolá nekik, hogy legyen
eszük; a mi bár nehezükre esett, de megfogadták. Azután a
kisasszonynak nyujtá kezét, s lesegitette a csónakba. Utána a többi
leány cselédet, meg a kis Gyuszit. Akkor engemet ott hagyott, s ő
maga házáig kormányozta a csónakot. Ott elhelyezve a kisasszonyt
és a vászonnépet: megint visszatért a férfihadért. Szakács, kukta,
vadász s más efféle kenyérvesztegető csónakra rakatott: ő ekkor
maga maradt hátra két lovász legénynyel. Azoknak megparancsolta,
hogy álljanak az ajtóragaszték alá, ha félnek a ház-omlástól. Hogy
harmadszor is visszatértem a csónakkal, akkor azt mondá: „no
Kampós; ez a ház nem állja sokáig, ha ledül, kirabolhatják. Innen
tehát minden szekrényfélét, a mi be van zárva, át kell szállitani az
ócska kastélyba; azt nem viszi el a viz.“ Azzal ő maga minden
szekrényt ládát gyürüjével lepecsételt, s áthordatott a régi házba, ott
állnak a padláson, jó helyen; mindent megtalál a méltóságos ur.
Mikor ezzel is elkészültünk, akkor az istállókból kivezetteté a
paripákat, s azokat a csónak után kötve, átusztattuk a magunk
házáig; ott azután egy lehordott ól tetejéből egy hidat csinálva, ugy
ugrattuk be az udvarra a töltésen keresztül: igen szép volt azt nézni.
Mig Kampós uram rövid kivonatban iparkodott a nap eseményeit
előadni, azalatt a két csónak megérkezett Garanvölgyi háza elé,
mely, mint kis sziget a tenger közepén, feküdt az árviz lepte téren.
Az ősi vert falnak most tünt ki a haszna; olyan volt az, mint a szikla:
még három lábnyira állt ki a vizből.
Az emlékezetes óltetőből készült hid szolgált állomási kikötőül,
azon lehetett, mint egy dobogón, az udvarra lejutni.
 XV.
A kik egymást nem ismerték.
A csónakok megérkezését nem fogadták valami csatánynyal, már
a hogy tudniillik szinpadon történt volna; átalános egymás nyakába
borulást scénázva impromtu; a minek az volt a legfőbb oka, hogy az
udvaron belől folyvást annyi volt a dolog, hogy éjfél tájon is talpon
tartá az embereket. A roppant, husz holdnyi tér, melyet az udvar,
park és szérüs kertek képeztek, mint egy körülkeritett sziget a tenger
közepén el volt lepve ökrökkel, lovakkal, birkákkal, miket a tanyákról
idehajtottak a viz elől, a béresek egy része azoknak
rendbentartásával foglalkozott, más része a cselédségnek
rözsekötegekkel erősité a töltést, a hol félteni lehetett; jó formán
észre sem vette senki a vendégek érkeztét, az ispánon kivül, kinek
erősen lelkére köté Kampós uram, hogy a csónakokat lakatra kösse,
s a lakat kulcsot a zsebébe tegye.
– Csakhogy itthon volnánk! Már most méltóságos uram, leszek
oly bátor, a kisasszonyhoz magam elvezetni; látom még ég a gyertya
a szobájában; ifju tensuram maga is oda talál az alatt az öreg urhoz.
Ankerschmidt kezet szoritott Aladárral, s a folyosón kétfelé válva,
egyik jobbra, másik balra tért. Mi tartunk Aladárral.
Az öreg ur is ébren volt még, midőn öcscse benyitott szobájába s
örvendve jött eléje.
– Hozott Isten! hogy jöttél ide?
– Egy lélekvesztőn. Ankerschmidtet is magammal hoztam.
– Azt ugyan jól tetted; a leánya agyonsirja magát apja után: azt
meg én hoztam ide. Fáradt vagy ugy-e?
 – Arról nem tudok semmit; hanem inkább szomjas. Hajnal óta
nem találtam vizet, pedig rajta jöttem.
– Tehát éhes is vagy? A vacsora kész.
– Hogy vártak vele ily későig?
– Kampósra vártunk, ki csónakkal körjáratot tett, hogy nincs-e
valahol veszedelem a faluban?
– Találkoztunk. Együtt jöttünk vissza. Ő riasztotta fel álmából
Ankerschmidtet, ki szerencséjére aludt azalatt, mig kastélya romjait
megkerültük s nem látta sokáig azt a pusztulást.
– A vacsora kész, de te válts öltönyt, mert kisasszony van a
háznál. Itt szobád kulcsa.
– Egy percz mulva készen leszek, szólt Aladár s az ismerős szoba
kulcsát átvéve, megölelé bátyját s eltávozott. Ugy tett, mint a ki
tudja, hogy otthon van.
Aladár, mig bátyja házánál hagyott ruhatárában válogatna,
elgondolá magában, hogy mégis szépen van az elintézve a világon,
hogy mikor egy embert minden porczikájában megtörtek, földhöz
csaptak, meggyürtek, eltettek, megtépásztak, megint kilöktek, akkor
az ember a legelső ellenségét, a kit előtalál, fölveszi a csónakjába,
reggeltől estig izzad vele, hogy hazahozza, szárazra tegye, s mikor
aztán már fáradtan, éhesen, szomjasan szeretne végig nyulni a
legelső szalmaágyon, akkor még szépen frakkot kell huznia, hogy az
ellensége leányától megkérdezhesse:
„Wie befinden Sie sich, mein Fräulein?“
Aladár semmi roszat sem kivánt a kisasszonynak magában; de
azt csakugyan nagyon szivesen hallotta volna, ha azt izené vala,
hogy nem jöhet a vacsorához, mert migraineje van, vagy már
lefeküdt.
 E várakozás azonban meghiusult; nem sokára hallá nagybátyja
szavait, ki őt sürgetni jött. Az étel az asztalon, a vendégek hiva
vannak.
Jól van, tehát essünk át ezen is.
Az öreg ur megrázta Aladár vállát s azt dörmögé neki: képzeld,
mintha abba a dalidóba mennél, a melyben a branyiszkói nap után
reggelig tánczoltál.
– Lehetett akkor; sugá vissza Aladár.
Ezzel az ebédlő felé siettek, melyhez egy közös folyosón keresztül
lehetett mind a két szárnyról jutni. Igy történt, hogy csaknem az
ajtónál találkoztak össze a lovaggal és leányával.
Ilyen szük helyen sokkal kevesebb czeremoniát lehet az
embernek egymással tenni, nem is nézheti senki, merre van jobb,
merre van bal? de meg a dolog természete is ugy hozza magával,
hogy a bemutatásokon hamar át kell esni, mert az ajtóban nem
lehet megállni.
Ankerschmidt egyik kezével leánya kezét fogta, másikat
szivélyesen nyujtá Garanvölgyinek s megrázta azt emberül.
– Uram, ön tudja azt, hogy én önnek mit tartozom köszönni?
– Semmit többet, mint a mennyit ön tett volna én értem hasonló
helyzetben.
– Én gyermekemet köszönöm önnek.
Ankerschmidt e szónál kénytelen volt leánya előtt tért nyitni, s a
mint e perczben Erzsike és Aladár egymással egyszerre szemközt
kerültek, a természethű gyermek hirtelen óvhatlanul odanyujtá kezét
Aladárnak, s e szókat rebegé:
– Én pedig önnek atyámat köszönöm.
 Ha e kéz reszketéséből, ha e hang csodálatos varázsából, ha e
szemek igaz bűbájából nem értett volna az ifju valamit, ugy nem
érdemelné, hogy egy ilyen tündértitku könyv még valaha nyitva
legyen előtte feledve.
A másik perczben már észrevette a leányka, hogy el hagyta
ragadtatni magát, s félénken huzta vissza kezét, és szemeit nem
merte többet felemelni azon arczra, melynek képe oly régóta él már
szivében.
Szerencsére az estebéd zaja, s Kampós uram kinálgatási kedve
hamar más irányt adtak a társalgásnak, ki is a bortól nem sokára jó
kedvet kapván, kezdett nagyon beszédessé válni. Máskor is az volt,
de most duplán.
– Csak azt az egyet sajnálom, hogy Aladár urfi nem volt itthon a
veszedelemkor.
– Miért öreg?
– Hogy maga szabadithatta volna meg a kisasszonyt. Ez már ugy
illett volna. Én azt regényben mindig ugy olvastam. Hiszen mink
öregek…
Aladár látva, hogy ez most mindjárt veszedelmes dolgokat fog
pengetni, belevágott a beszédébe.
– Oh azért én is követtem el utközben hős tetteket, a mikről
valaha regényt lehet irni; én is mentettem meg veszélyben forgó
lényt a végső pillanatban.
Ankerschmidt gondolá magában; no ez a fiatal ember szereti
itthon elmondani a viselt dolgait, bizonyosan a megmentett
népségről; ha szereti, hát tegye.
– Hol? kit? kérdé mohón Kampós uram; ki szörnyen kapott rajta,
hogy Aladárnak egyszer már a saját szájából authentice hallhatja
egy hős kalandját.
 – Hát a jegenyesen tul – egy ürgét. Szólt Aladár mosolyogva.
– Ah. Oh. Hangzott több oldalról is a kedvetlen észrevétel. Maga
Ankerschmidt is megrestelte a dolgot s sietett helyreigazitani a
tudósitást.
– No, azt elhallgatja fiatal barátunk, hogy a jegenyésen innen
meg vagy ezer embert szabaditott meg egy erőfeszitéssel és egy jó
ötlet által.
– Ah, könyörgöm alássan, hogyan volt az, tessék elmondani!
szabadék Kampós ur, nagyon rajtaesve a hangon.
(Dehogy nem, gondolá magában Ankerschmidt; majd itt a
leányom előtt, hogy még jobban belé szerelmesitsem; már akkor
csak inkább beszéljünk az ürgéről).
– De valjon hova is lett a mi kis ürgénk? egészen elfeledkeztem
róla a nagy hevélyben: kérdezé Aladártól.
– Ott alszik a köpenyem zsebében most is, szólt Aladár; menjen
Kampós ur, hozza el.
– Mit? Én? Egy ürgét? kiálta felugorva a puritán férfiu. Mondja a
tekintetes ur, hogy hozzak el egy oroszlánt, egy bölény-bikát
elhozom; de egy ürgét! a nyavalya törne ki, ha hozzá kellene érnem.
Nincs ahoz fogható utálatos állat a nap alatt.
– Oh ne mondja, könyörge érte Erzsike; én olyan szépnek
találom.
– No lássa; biztatá Aladár, a kisasszony szeretné látni.
Csunyának már nem merte ezután állitani Kampós uram; de rá
fogta, hogy harap; – hát Aladárt mért nem harapja meg? Az más. Az
neutralis; de őtet megismeri; mert ő dijt tüzött ki az ürge familia
kiirtására. Őtet harapta már meg farkas is, fel se vette, de az ürge
harapásától meghal.
 – Jól van no, hát majd érte megyek magam, szólt Aladár, s
rögtön felugrott az asztaltól s két percz mulva visszatért.
– Aha! kiálta Kampós uram, nem látva a visszatérő kezében a
fertelmes fenevadat; nincs meg ugy-e? Elszökött azóta, lyukat furt a
ház alá, abba elbujt, már most az ott el fog szaporodni s alámínázza
az egész kastélyt.
– Itt van biz az a kabátom ujjában, szólt Aladár s elővette az ott
magát rögtön elhelyezett állatocskát s tenyerébe fekteté. Ni hogy
bámul a gyertyába.
– Oh be gyönyörü kis állat; monda Erzsike, gyermeteg örömmel
kapva a tréfás állatocskán; milyen szép fekete szemei vannak!
Aladár aztán oda vitte hozzá a kis polgártárst; Erzsike
megczirógatta azt sima kezecskéjével.
– Hozzá ne nyuljon kisasszony, meglássa szerencsétlenül jár; óvá
a gyanutlan lelket a tapasztalt férfiu, Kampós. Jaj ha én hozzám
olyan közel volna, engem a láz futna végig.
Erzsike is érzett akkor valami delejes lázt átfutni idegein, a
közelléttől, – de nem az ürgéétől.
A bizalmas kicsi állat lassankint Aladár kezéről a czirógató kézre
kapaszkodott át, s onnan lassan felmászott a habzó musselinon, fel
egész a válláig, ott a bámulatos szép gömbölyü elefántcsont halomra
leült; be jól kiválasztotta a helyét az ördögtől született.
Kampós uramnak valóban halavány lett az arcza e látványra, mig
Erzsike gyönyörködve tekinte a játékos vadállatra; Aladár is
gyönyörködve nézett oda: talán nem is az ürgére; Ankerschmidt
pedig sajnálta már, hogy ezt a themát elő találta hozni.
– Megeszi-e a kenyeret? tudakolá Erzsike, próbára egy falatot
törve számára.
 – Meg bizony! erősité kasznár ur, egész familiája a kenyerünkön
osztozik; azt sem várja, hogy megsüssük és kináljuk vele; elébb
eszik belőle, mint mi magunk.
A kis kenyérpusztitó el is vette mohón a falatot s a szék támlájára
szökve vele, ott mókusok módjára nyakába kapta bolyhos farkát s
elkezdett a kezéből élni: hogy azt még az öregek is megnevették.
– Adja ön nekem ezt a kis jövevényt: könyörge Erzsike
Aladárnak.
– Szivesen.
– Hanem jó erős kaliczkát csináltasson neki, nagysád, sürgölé
Kampós ur, mert ez keresztül rágja a tölgyfát is.
– Ah! Ki tartaná kaliczkában a vendéget. Nálam szabadon kell
neki járni.
Ebbe aztán Ankerschmidt is beleszólt.
– Gondold meg leánykám, hogy most magunk is vendégek
vagyunk, s a mit ugy hinak, hogy „nálunk,“ az a viz alatt van.
– Oh nem uram: igazitá őt helyre az öreg Garanvölgyi. Az én
vendégem otthon van a házamban. Azt akarom, hogy önök idehaza
találják magukat nálam mindaddig, mig kastélyukat ujra fölépithetik.
Tanyám elég tágas; s én ugy is egyedül vagyok.
E szónál gyöngéd szemrehányással tekinte Aladárra; s e szóra
nagy elhallgatás történt.
Az ilyen perczekben szokott az megtörténni, hogy mindazok, a kik
ugy elhallgattak, egy dologról gondolkoznak.
Leghamarább Ankerschmidt töré meg a csendet.
– Igen köszönöm önnek szives ajánlatát s nehéz volna okot
találnom rá, a miért visszautasitsam. Erzsike ugy is „bácsi“nak hija
már önt.
 – Oh, ön jól tudhatja, hogy a mi ismeretségünk nagyon régi
keletü. Én Erzsi kisasszonynak régi lekötelezettje vagyok. Ő is
mentett meg engemet, pedig akkor még nem is tudta, hogy valjon
érdemes leszek-e rá?
– Mi volt az? kérdezé Aladár, Erzsikére tekintve.
– Oh semmi. Tréfa. Rebegé a gyermek, szépen elpirulva.
– De rám nézve komoly dolog volt az; monda Garanvölgyi.
– Hogyan, uram! szólt a hadastyán, poharát letakarva tenyerével,
hogy Kampós uram orozva tele ne tölthesse. Ön emlékeznék még
ama bohóságra?
– Oh igen, még most is meg van nálam a levél, melyet először
nem akartam elolvasni, s melyért másodszor tisztelt szomszéd uram
le akarta vágni a fejemet, s melyet végtére azóta is mindig a
tárczámban hordozok.
Azzal, hogy állitásáról mindenkit meggyőzzön, elővonta régi
bőrtárczáját s annak negyedik rejtekéből, hol legrégibb ereklyéi
álltak: egy pár magyar feliratu bankó anno elmult jó időből, egy
kopott arczkép, egy selyem rongy valami zászlóból stb. stb., onnan
vette elő a gondosan megőrzött levelkét, melyet a gyermeklyánka irt
hozzá titokban, hogy őrizkedjék a házi árulótól.
A levelet Aladárnak nyujtá, a többiek ugy is tudtak felőle.
Hanem egyet nem tudtak a többiek: azt, hogy Aladár e levél
irásáról rá fog ismerni arra a kézre, mely a szabadságát visszaszerző
folyamodást irta. Azt egyik sem sejtheté, hogy ő e folyamodást látta
már valahol.
Aladár minden csepp vérét szivéhez érzé tódulni, midőn e levelet
megpillantá; nem olvasta ő, mit tartalmazhat, vagy tán olvasta is, de
nem gondolt reá; e vonásoknál azon sorok álltak szeme előtt, mik
gyermeteg őszinteséggel könyörögtek egy mindenkitől, saját
magától is elhagyott, elfelejtett veszendő fogolyért.
 Tehát ez a kéz, ez a sziv volt az, mely csak tenni, és érezni tud,
de nem enged magára találni? Tehát nem a kik ugy mosolyognak
már messziről, hanem a ki beteszi az ablakot, mikor arra jönni látja;
az volt a valódi?
– Nos, nem adod vissza a levelemet, vagy meg akarod
könyvnélkül tanulni? kérdé az elmélázottat Garanvölgyi.
– Azon gondolkozom, hogy ez irás ugy hasonlit – más valakinek
az irásához.
E pillanatban Aladárnak lehetetlen volt észre nem venni azt a
megdöbbenést, melylyel egyszerre pillantottak egymásra
Ankerschmidt és leánya; a leányka azután mily zavarodottan süté le
szemeit, míg Ankerschmidt alig tudott nyugalmat tettetni többé.
– Hjah öcsém, szólt Garanvölgyi visszatéve a levelkét ereklyés
rejtekébe, egyforma kézzel irnak sokan; egyforma szivvel kevesen.
Ankerschmidt nyugtalanságát Garanvölgyi arra magyarázta, hogy
a nap fáradalmai után nyugalomra vágyik, azért jelt adott a
felkelésre, a mit mindenki bucsuvételre használt, s nehány percz
mulva mindenki szobájába sietett.
Aladár éjszakai nyugalmáról ugyan nagyon roszul volt
gondoskodva ama levélke megmutatása által; az éjszakát jobban
átábrándozta, mint átaludta.
Ki tudja, tán van valami abban a babonában, a mit fiatal lyánkák
tartanak, hogy ha kedvesükről álmodnak és fölébredtek,
megforditják a vánkost fejük alatt, s akkor a kedvesnek kell a
lyánkáról álmodni. S az álom tündére bübájos tündér.
Garanvölgyi elbámult, midőn jókor hajnalban fölkelve, csendesen
lábhegyen lépdelt végig a folyosón, hogy az alvók felzavarása nélkül
juthasson ki az udvarra, a külső veszélyt megtekintendő; s már akkor
Aladárt egészen felöltözve látta szobájából kilépni.
– Hát te már fölkeltél?
 – Igen; jókor elakarok menni.
– Menni? Hová? és min?
– A lélekvesztőn, a min jöttem; valahová, a hol hasznomat
vehetik.
– De hát miért ily sietve?
– Menjünk szobájába bátyám. El fogom mondani.
Az öreg ur visszament Aladárral szobájába.
– Nos, mond el hát, ki kerget?
– Kedves bátyám, tegnap, midőn azt a levelkét megmutatta; én
annak vonásaiban ugyanazon irásra ismertem, melyet azon
ismeretlen folyamodáson láttam, a mi szabadságomért sikeresen
esdett.
Garanvölgyit magát is nagyon meglepte e fölfedezés.
– E szerint e leány irta volna azt is.
– Igen. És én már most többet tudok, mint a mennyire
szükségem van.
– És most azért elakarod hagyni a házat.
– Mit tehetek mást? Egy nővel találkozom életemben először, a
kinek szive van. Ha öreg asszony volna, örülnék rajta, mert azt
mondhatnám neki: „édes anyám!“ s kérném, hogy nevezzen fiának.
De egy szép, okos, érzelmes gyermek és én: minek találkozunk mi
össze?
– Én nem látok benne semmi veszedelmet. Ha egymásba
szerettek, elveszed s neked adják.
– Jó bátyám; én szegény legény vagyok; fáradsággal keresem a
kenyeret. Ezek gazdagok. Ha én most itt maradok; a hol nem ő
rajtuk áll, hogy engem elfogadjanak-e vagy sem? midőn az árviz
őket épen hozzánk kergette, s nincs módjukban, hogy ha akarnak,
elutasitsanak; hanem kényszeritve vannak egy födél alatt lenni
velem, s ha nem akarnak látni, nem akarnak hallani, még csak azzal
sem segithetnek magukon, hogy itt hagyjanak, mert köröskörül
tenger van! és, ha én még is felhasználom ezt a szomoru helyzetet,
és itt maradok; nem jutok-e egy erkölcsi értékbe azzal a Karaib
szigeti indiánnal, ki a hozzámenekült hajótörteket megeszi?
– Igazad van; eredj.
Az öreg ur megszoritá öcscse kezét s még egyszer azt mondá
neki: „eredj:“ azzal karjába fogódzott s ki ment vele az udvarra
további intézkedéseket tenni.
A cselédek tudósitásai szerint az éjjel a szél nagyon
veszélyeztette a töltéseket. Aladár rögtön intézkedett, hogy nehány
hombár, melyet megraktak kővel, oly hevenyészett sarkantyút
képezzen a töltés előtt, melyen a hullám rohama megtörjék; mire e
munka készen volt, eljött a reggelizés ideje; s ott még egyszer kellett
találkoznia Aladárnak Ankerschmidtékkel.
Aladár minthogy szökve nem mehetett el a háztól, bucsuzás
fejében megmondá Ankerschmidtnek, hogy ismét csónakra ül, és ha
lehet felevez Tisza-Dobig; a hol a romlás eredete van.
– Mit használhat ön ott most? kérdé tőle Ankerschmidt, hogy
ellenkezzék vele.
– Semmit; de legalább tanulmányozhatok.
– Én pedig arra számitottam, hogy ma reggel kirándulást teszünk
a külső tanyákra.
Ez marasztalás volt in optima forma; a mit nem lehetett
elutasitani.
– Nem sietős az utam; nem bánom, ha kicsónakázunk, az idő
szép.
 Az öreg ur puskát is akart magával vinni, jó alkalom kinálkozván
vadászatra: de Erzsike lebeszélte róla. Minek az? vagy magát vagy
„valakit“ megtalálna még vele lőni.
Aladár körülhordta a csónakot ez uttal az omlott kastély
mellékén, mely bámulatos szépen összevissza volt roskadva;
Ankershmidt káromkodott mindenféle nyelven, minden „teremtette“
és „Kreuzsakerment“ után bocsánatot kérve utitársától az illetlen
szóért. Aladár biztatta, hogy csak tessék, az tisztitja az embert; azért
a magyar ember kedélye olyan traktabilis, hogy kikáromkodja magát,
nem tartogatja sokáig.
– No, csakhogy magunk megvagyunk – szólt végre a hadastyán,
megnyugodva; menjünk a mezőre, akarom mondani: a tengerre.
Azzal zsebkendője szegletébe egy bogot kötött; mely alkalommal
Aladár észrevevé, hogy ugyanannak a másik három szeglete is
csomóba van már kötve. Nem állhatta meg, hogy meg ne kérdezze,
hogy mire való lesz az?
– Ez a csomó, a mit most kötöttem? Ez arra emlékeztet, hogy
legközelebb, a mint Grisák barátommal összejövök, annak a hajába
kapok s megkérdezem tőle, miféle derék emberrel épittette fel a
kastélyomat? Ez a másik csomó amice Mikucseknek szól, hogy mi
keresete volt a töltés hosszában a mult éjjeleken? Ez a harmadik
Bräuhäusel ur számára van kötve. No iszen azt a spektáklit kell majd
megnézni, a mit én ott csinálok, ama bizonyos protectio utján készült
zsilipért.
A negyediket elhallgatta.
– Hát a negyedik?
– Az? Azt csak ugy kötöttem, véletlenül; az nem jelent semmit.
Délig sok szép vidéket be lehete csónakázni; néhol a határkő
meglátszott a vizben; ott Ankerschmidt megjegyzé: itt kezdődik az
én földem.
 Egy helyen azonban szép dombos emelkedés volt, az mint sziget
állt ki a tengerből, ottan kikötött Aladár.
A domb árpával volt benőve, mely gazdag négysoros kalászait
már kihányta, az egész tér lehetett ötven lépés körüljárva. – Azon
elbizonyoztak mind a ketten, kié lehet az a menekült föld?
Ankerschmidt azt állitá hogy Garanvölgyié, Aladár Ankerschmidténak
mondta.
– Akárkié, vigyünk haza belőle mutatványt, hogy ime zöldet
láttunk, mint a Nóé galambjai.
Azzal Ankerschmidt egy marok árpát leszakasztott; Aladár is
leszedett kilencz szálat s a kalapja mellé tüzte.
– Tenger biz ez; szólt a lovag, széttekintve a sik viz felett. És
most elmondhatjuk, ifju barátom, mind a ketten, hogy birtokaink egy
helyen vannak, az enyim is a tenger fenekén, mint az öné.
– Minden hasonlitás sántit.
– Az enyim nem sántit. Most én sem juthatok a földemhez, ön
sem: ez homogen eset; a mikorra én az enyimhez juthatok, akkorra
ön is hozzá fog jutni a magáéhoz.
– Hogy érti ön ezt?
– Bizonyosan tudom, hogy ön kegyelem utján vissza fogja kapni
elkobzott jószágait.
Aladár fejében egy gondolat szikrája villant meg.
– Ha ön ezt tudja, uram, akkor azt is tudni fogja, kinek
köszönhetem e nem remélt kegyet; kérem, adja át neki e forró
kézszoritást.
Ankerschmidt észrevette, hogy Aladár előtt többet talált elárulni,
mint a mennyit akar s sietett hevesen tiltakozni.
 – Ifju barátom, én kijelentem önnek, hogy kegyet csak annak
köszönhet ön, a kitől jön. E leczkét tőlem, mint vén katonától, vegye
jó néven; s ne keressen titkos pártfogókat, a mik önnek nincsenek.
Aladár megköszönte a tanitást; eleget tudott már.
E hir uj eszméket öntött szivébe. Nem a birtok öröme volt az;
Aladár, mint minden igaz gavallér, jól tudta azt, hogy a birtok csak
kötelezettség, s a ki éveinkben Magyarországon terjedelmes földnek
ura; annak kötelessége megszámlálhatatlan, s ahhoz mérve a
legterhesebb foglalkozás is valóban sinecura! hanem boldoggá tette
az a gondolat, hogy többé nem nevezheti senki önzésnek azt, a mi
szerelem.
És boldoggá tette az a gondolat, hogy keresztül látott egy család
jellemén, melyet eddig nem ismert.
Egy gyermek, angyali részvétből, nem érdekből, nem is női
hajlamból, hanem csupán a jóknak azon ösztönéből, mely az érző
lelket a szenvedők felé hajlitja, megóvni igyekezik egy öreg embert,
akkoriban nagyon járványos veszélytől. Ez öreg embernek szeretett
rokona van, ki státus-börtönben sinylik; kit mindenki elfelejtett, s
kiért az öreg maga nem tehet semmit, mert minden lépésével csak
ártana neki; az idegen ur gyermeke titokban folyamodást ir érte; az
apa nem haragszik ezért, maga eljár vele; meglátogatja a foglyot
börtönében, ott gorombáskodik vele, nehogy az sejtse, ki hozta el
szabadulása olajágát; itthon elzárja előle leányát, nehogy
megszeressék egymást s valaki azt mondhassa, azért esdett a trón
előtt, ősz érdemeire hivatkozva, egy elitélt vagyonának
visszaadásaért, hogy azt saját leányának szerezze meg. Ezért utasitá
el a látogatót az első találkozás után, s ovakodott vele
összeköttetésbe jönni.
S nem is történt volna az meg soha, hogy egymást megismerjék,
ha csak a romboló árviz egy kis szigetre össze nem sepri
mindnyájukat.
 Aladár visszatértiben nem találta oly szemetesnek a viz felszinét,
mint eddig.
Mit nyom az mind, a mi a földön elveszett, ahoz mérve, a mit a
sziv nyert?
Délre haza jutva, legelébb is Kampós uram azzal az örvendetes
hirrel fogadá őket, hogy mig oda voltak, az alatt az ár két hüvelyket
apadt.
Aladár nem örült már annak; s még beleveszett a kasznárba,
hogy mit tud ezen ugy jubileálni, mikor ez kétségtelenül arra mutat,
hogy másutt uj gátat szakitott az ár, s más vidéket is elöntött.
Erzsike kijött atyja elé, kinek Aladár megmentett paripáit
mutogatta meg az akolban, s onnan atyja karjába füződve, ment fel
a lakházba. Fején rózsaszin szalagos szalma kalap volt vadrózsa
bimbókkal, miket a kert sövényéről tépett.
Garanvölgyinek mindjárt feltünt, hogy Aladárnak jobb kedve van;
mint reggel volt. A helyett, hogy az ő szobájába jött volna,
elbeszélni, hol járt s miket látott? kinn marad a folyosón, s mintha se
árviz, se veszedelem nem volna, Ankerschmidt leányával cseveg és
nem borzad a Karaib sziget lakójának étvágyától, ki a hozzámenekült
hajótöröttet megeszi.
Az ebédlőben az asztalra téve egymás mellett volt Aladár kalapja
az árpabokrétával s Erzsikéé a vadrózsabimbókkal. Garanvölgyi
megszámlálta az árpaszálakat, kilenczen voltak; a rózsákat is, az hét
volt.
Nem sokára Erzsike atyjához távozott, s az után Aladár is csak
felkereste nagybátyját, s a csengetyü szavára mind a négyen
összetalálkoztak ismét az ebédlőben.
Garanvölgyi megint megszámlálta az árpaszálakat: – az csak
nyolcz volt; aztán a rózsabimbókat; – csak hat volt már.
(Ezek már egymást l o p j á k ! Gondolá magában az öreg ur.)
 Bátran fogadhatott volna rá, hogy a hiányzó árpaszálat valahol
Erzsike imakönyvében, a rózsabimbót pedig Aladár tárczájában lehet
megtalálni.
A mint Aladár egyedül maradhatott nagybátyjával, azonnal közlé
vele, a mit Ankerschmidttől hallott birtokának visszanyerése felől.
– Sajnállak érte, szegény fiu; monda rá az öreg keserüen. Milyen
szépen meg voltál már abban nyugodva, hogy „volt, nincs.“ – „Több
is elveszett már Buda alatt.“ Sok ilyen példabeszéd van a
magyarban. Tudom, hogy keveset álmatlanitott az a gondolat, hogy
hát ha még egyszer lenne! Szereztél magadnak kenyeret,
megszolgáltad, beérted vele. Helybentaláltad magadat ez uj életben
s hozzászoktál, hogy a mi nincs, az nem kell! – És most egyszerre
kapsz egy darab Amerikát! Kasznárom ott járt három izben hajdani
jószágodon, s elmondta, hogy miket tapasztalt. – Nyolcz év alatt
négyféle bérlője volt a jószágnak; mind a négy azon volt, hogy a
jószágot elpusztitsa; három megszökött, a nélkül, hogy az államnak
haszonbért fizetett volna. Elég, ha a budgetben ott figuráltak a
tételek. Szép mürzthali tehenészeted, merino juhnyájad, vérlovaid
még a legelső bérnök elprédálta, a második elprédálta gonddal
ültetett erdődet, parkodat kimérte ölfának; az utolsónak már nem
maradt más, mint a házon levő redőnyöket eladni. Ez az élelmes
ember, még az üvegházadon levő ablakokat is értékesitette. Mikor
Kampós legutoljára ott járt; persze ugar sem volt már hagyva; s a
halomra gyült trágyát épen akkor adta el a bérlő szomszéd határbeli
parasztoknak. Benn a házban egy szék nem volt, a mire leüljön
valaki; hanem annál inkább teli egér lyukkal minden szeglet. Az
ablakokban négy-öt emeletet csináltak maguknak lyukakból a
patkányok, ugy megszerették a helyet, s a czimertermed plafondján
keresztül csurgott az eső. Most ezt a „prairiet“ átveszed; mely mikor
elvesztetted, megért beruházásiddal háromszáz ezer forintot, most is
meg ér kettőt. Van rajta husz ezer forint adósságod, annak nyolcz
esztendő óta persze senki sem sem fizette a kamatját. Legelső
dolgod lesz valami jótékony bankárt fölfedezned, a ki megszán, s
keresztyéni harminczhárom percentre honorálja váltóidat vagy
tizezer forintig. Akkor aztán törheted a fejedet, hogy mit kezdj vele
előbb: szántóvető állatokat végy-e? a házadat tatarozd-e? vagy a
kamataidat törleszd, nehogy a tőkét felmondják? Azért még egyszer,
kedves öcsém, fogadd őszinte sajnálkozásomat.
– Nem az itt a főkérdés, szólt Aladár vállat vonitva.
Persze, hogy nem az volt a főkérdés: hanem az, hogy ha fáradni
és küzdeni kell, lesz h o l ? és lesz k i é r t ?
Tudta ezt az öreg ur maga is. Ugy olvasott ő Aladár lelkében,
mint a kinyitott könyvben.
Aladár az nap ott maradt, hova is indult volna már olyan későn?
Másnap ismét annyi dolgot talált a faluban, hol az egyes házak itt
ott engedtek az árnak, hogy dél vetette haza a nagy munkából;
délután eltölt az idő szelidebb tracirozással. Két sziv összeköttetési
vonalainak előmunkálatai voltak azok, mikre csak a felsőbb helyről
nyerendő helybenhagyás hiányzott még.
Dehogy gondolt az elutazásra többé. Az ugyan jól esett volna
neki, ha valaki marasztalta volna; hanem a helyett nagybátyja
szüntelen azzal a sarcasmussal faggatta, hogy „mikor indul már a
vizár pusztitásait tanulmányozni? várja-e, mig érdekesebb lesz a
stadium?“ Legfeljebb Erzsike ejtett olyan czélzásokat, hogy azon a
kis csónakon járni nagyon életveszélyes lehet.
Három nap multán azonban már maga is átlátta Aladár, hogy
miután kimondá, hogy el fog menni, tovább csakugyan nem
maradhat, ha szavainak hitelességét tökéletesen kompromittálni nem
akarja. Este tehát kijelenté bátyja előtt, de ugy, hogy mellesleg a
többiek is hallhatták, hogy holnap reggel csakugyan utra kel, csak
egy evező legényt visz el magával.
Garanvölgyi azt mondta rá, hogy jó lesz, majd süttet neki az utra
pogácsát.
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