RSC Advances

View Article Online

REVIEW View Journal | View Issue

Acyclic and cyclic imines and their metal

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Cite this: RSC Adv., 2018, 8, 23294

complexes: recent progress in biomaterials and
corrosion applications
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Wail Al Zoubi, a Saad Gomaa Mohamed, b Abbas Ali Salih Al-Hamdani,c

Agastya Prastita Mahendradhanya and Young Gun Ko*a

This review describes the contemporary development applications on scientific areas of acyclic and cyclic
Schiff bases and their complexes with an emphasis on the author’s contribution to the field. After a short
historical introduction, this manuscript is divided into two main parts. In the first section, Schiff bases are
reviewed for their biological activities including antibacterial, antifungal, antioxidant, cytotoxic, and
enzymatic activities as well as their interaction with single-stranded-DNA which have shown remarkable
activities in each region of research. The second part deals with the corrosion of metal and its alloys in
Received 4th March 2018
Accepted 6th June 2018
corrosive environments and their organic inhibitors. The main section of this part is to investigate the
different chemical structures for Schiff bases used in such aggressive solution to protect metals.
DOI: 10.1039/c8ra01890a
Knowing the maximum corrosion efficiency or bioactivity of a specific chemical structure in a specific
[Link]/rsc-advances application environment is helpful for choosing the most appropriate compound.

groups SBs possess an important position in the biological

1. Introduction eld.24,25 As a consequence, a broad research eld dealing with
The term Schiff base (SB) comes from the name of Hugo cyclic and acyclic SBs and their metal complexes has led to an
Schiff,1,2 German by nationality, who prepared the rst so-called extensive number of works, and has been comprehensively
Schiff base in 1864.3,4 Schiff bases (SBs) contain the azomethine studied in 201726 and 1987.27 In 2004, Hernandez-Molina and
group (–RC]N–) and are typically synthesized by condensation co-workers28 also reported some classical synthetic methods of
reactions of an active carbonyl compound with a primary asymmetric SBs derived from diaminomaleonitrile and their
amine. They are considered to be a promising candidate for Zn, Cd and Cu complexes. This provides a more general over-
a variety of applications related to biological activities (such as view of the chemical synthesis of SBs, the preparation of various
antiapoptotic, antifungal, antibacterial, anti-inammatory and corresponding metal complexes and their different applica-
antiviral activities),5–7 catalytic activities,8–13 electroluminescent tions. The main goal of this work is to give a complementary yet
properties,14–16 uorescence properties,17–19 nonlinear optical more detailed overview on acyclic and cyclic SBs and their metal
(NLO) properties,20 and applications in electrochemical complexes, focusing strongly on compounds for their applica-
sensing21 and organic photovoltaic materials.22 Owing to the tion as bioactive components and organic inhibitors. On the
ease of preparation and tunability of their stereo-electronic other hand, this review paper also focuses on organic inhibitors
structures, most SBs are attractive ligands because they in corrosive environments and not inside the coatings. There-
readily form stable complexes with most metal ions.23 In addi- fore, we try to collect main experimental results of researches
tion, SB ligands are able to coordinate with various metal ions about metal corrosion inhibition in different Schiff bases, to
thus stabilizing them in different oxidation states, and, there- present comprehensive insight for researchers with appropriate
fore they are among the most important ligands used in current categories and to provide guidance for future studies in this
coordination chemistry due to their well-known coordinative eld.
capability. Due to imine (CH]N), hydroxyl (OH) and other

2. Biological and anti-corrosion

a
Materials Electrochemistry Group, School of Materials Science and Engineering, applications of acyclic and cyclic Schiff
Yeungnam University, Gyeongsan 38541, Republic of Korea. E-mail: wailalzoubi@
[Link]; younggun@[Link] bases
b
Mining and Metallurgy Engineering Department, Tabbin Institute for Metallurgical
Studies (TIMS), Tabbin, Helwan 109, Cairo 11421, Egypt Azomethine or imine groups present in the organic compounds
c
Department of Chemistry, College of Science for Women University of Baghdad, have been shown to be critical to their biological activities. In
Baghdad, Iraq addition, the presence of nitrogen and oxygen donor atoms in

23294 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

such compounds makes them structurally similar to neutral active in protecting DNA against cOH radicals in a concentration-
biological systems and they are utilized in elucidating the dependent way, i.e. DNA defense is increased with the increase in
mechanism of transformation of racemization reactions.29–31 the concentration of the test compound. In addition, SBs
Various biological activities are considered due to the presence exhibited signicant activity against brine shrimp nauplii.34,35
of the azomethine linkage (>C]N–) present in living systems.32 Further, the prepared SBs and their complexes seem to be able to
On the other hand, for anti-corrosion, the corrosion inhibition combine with the lipophilic layer in order to enhance the
properties of these compounds can be assigned to its molecules membrane permeability of biological applications.
with p-electrons of the imine group and p-electrons of aromatic On the other hand, the incorporation of heavy metal ions
substituents. such as Ni(II) and Pd(II) triphenylphosphine (Scheme 2) in tri-
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

dentate SBs has been successfully carried out. The organome-

tallic moieties clearly improved the biological performance, e.g.,
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

2.1. Biological activities of acyclic and cyclic Schiff bases in antimicrobial assays Ni(L1)PPh3 exhibited dual inhibition
Schiff bases and their complexes are considered as a special against bacterial and fungal strains whereas for the rest of the
category of compounds owing to their biochemical synthesis, compounds varying the degree of activity was examined against
antimicrobial, antifungal, electrochemical analysis as well as different strains. The prepared compounds have shown a high
catalytic activities.33 Therefore, various SBs forming metal tendency for DNA binding either through intercalation or
complexes have been comprehensively studied, exhibiting a groove-binding nature which displays the mechanism of the
a broad range of applications, especially in biological systems. antitumor effect of these metal complexes. These ndings
The study of SBs and their complexes reveals their interesting support the view that some of these compounds can be prom-
spectral properties which are helpful in understanding the ising candidates for drug formulation and development due to
various features of the coordination chemistry of metal ions. On their diversity of bioactivities.36
the other hand, previous works performed in the last decades Shujah et al.37 have reported the synthesis and bioactivity of
have recognized the ability of SBs and their complexes to exert dimethyl (1), diethyl (2), diphenyl (3), di-n-octyl phthalate (4), di-
various bioactive effects either in vitro or in vivo. Details on these tert-butyl (5), and n-butylchlorotin(IV) (6) derivatives of N0 -(2-
applications are given below. hydroxy-3-methoxybenzylidene) form hydrazide ligand
2.1.1 Schiff bases containing aromatic moieties. Shabbir (Scheme 3a–c). These compounds are either mononuclear in
et al. have reported the synthesis of four Schiff base Cu(II) which the Sn atom is in a distorted trigonal bipyramidal geom-
complexes, i.e. bis((E)-2-((4-phenoxyphenylimino)methyl)pheno- etry (a and c) or homobimetallic with each Sn atom in
late) copper(II) (Cu(L1)2), bis((E)-2-((4-(4-biphenyloxy)phenyl- a pentagonal bipyramidal environment (b). This behavior can be
imino)methyl)phenolate) copper(II) (Cu(L2)2), bis((E)-2-((4- assigned to the steric factor and the high lipophilic character in
(naphthalen-1-yloxy)phenylimino)methyl)phenolate) copper(II) the former. These factors, planarity and low molecular weight,
(Cu(L3)2) and bis((E)-2-((4-(2-naphthoxy)phenylimino)methyl) which facilitate smooth diffusion were presumably turned into
phenolate) copper(II) (Cu(L4)2) (Scheme 1). Biological researches the high activity of diphenyltin(IV) complexes (3). Besides, the
(cytotoxic and antitumor) have shown that these complexes are chemical structure suggests that the H/N, H/p and p/p
bioactive in these environments. Therefore, the SBs are highly interactions play a seminal role in generating fascinating

Scheme 1 Synthesis of Cu(II) complexes [Cu(L1)2–Cu(L4)2].

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23295
 View Article Online

RSC Advances Review

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Scheme 2 Synthesis of complexes M(L1)PPh3–M(L4)PPh3.

Scheme 3 Synthesis of Schiff base complexes (a–c).

supramolecular structures. Therefore, ON donor imines (E)-2-((4- respectively. The biological ndings showed signicant activity
phenoxyphenylimino)methyl)phenol (HL1), (E)-2-((4-(4-biphenyloxy)- in protecting DNA against hydroxyl free radicals in a concen-
phenylimino)methyl)phenol (HL2), (E)-2-((4-(naphthalen-1- tration dependent manner. It is thought that these ligands at
yloxy)phenylimino)methyl)phenol (HL3) and (E)-2-((4-(2-naph- different doses could be used against different cancer-
thoxy)phenylimino)methyl)phenol (HL4) (Scheme 4) have been chemopreventive models and could seem to contrive safer
prepared. The experimental results of brine shrimp cytotoxicity medical treatments for future. In addition, the results indicated
assays showed (lethal dose, 50%) LD50 values of <1 mg ml1 that the one-electron irreversible oxidation product is formed
exhibiting signicant antitumor activity and with (half maximal due to hydroxyl moiety and that the process is diffusion-
inhibitory concentration) IC50 values of 14.20 and 4.54 mg ml1, controlled.38

23296 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Scheme 4 Synthesis of imines (HL1–HL4).

In addition, three SBs complexes of Co(III), viz. [Co(L1)(N3)2] Zn(II), Cd(II) complexes have been prepared and studied in
(1), [Co(L2)2(N3)2]NO3 (2), and [Co(L3)2(N3)2]ClO4 (3), where different physicochemical studies. The bioefficacy of SBs and
H2L1 ¼ N,N0 -propane-1,3-diylbis[1-(pyrrol-2-yl)methanimine], their complexes have been evaluated against the growth of
L2 ¼ 1-[(thiophen-2-ylmethylidene)amino]propan-2-amine and (Staphylococcus aureus and Escherichia coli) bacteria in vitro to
L3 ¼ 1-[(3-methylthiophen-2-ylmethylidene)amino]propan-2- assess their bioactivity potential. The improved activity of the
amine (Scheme 5), have been prepared and characterized. The metal complexes might be attributed to their increased lipo-
syntheses have been achieved by the reaction of Co(II) ions with philic environment arising due to chelation. Besides, the
the tetradentate Schiff base (H2L1) or the bidentate ligands L2 increase in lipophilicity enhances the penetration of SBs and
and L3 in the presence of azide. Structural studies reveal that all their metal complexes into the lipid membranes and thus
of the complexes comprise a CoN6 chromophore in which the restricts further growth of the organism. Also, the SBs and their
central Co(III) ions adopt a distorted octahedral geometry. metal complexes are more toxic to S. aureus than to E. coli,
Whereas compound (1) is a binuclear end-on bis(m-azido) probably due to the sulfonic OH, OCH3, S and CH3CH2CH
complex, both compounds (2) and (3) are mononuclear with two groups, which might interact with the double membrane. This
terminal azide ions in cis positions. The antibacterial activity of activity is related to the nature and structure of the complexes.40
all the complexes and their constituent Schiff base ligands has SB complexes containing copper ions reveal surprising
been tested against some Gram (+) and Gram () bacteria. From molecular diversity, not only in coordination geometry but also
these results, it could be concluded that the previous in more subtle changes in the ligands. These ligands with
compounds have mild to strong bactericidal properties which copper ions represent a class of compounds with the most
increase with amount to some extent. However, none of these interesting properties, from the point of view of both chemical
compounds is as potent as commercial antibiotics like cipro- and biological behavior. In this regard, Cu(II) complexes
oxacin at similar concentrations. These results of the work prepared from the condensation of S-methyl- and S-benzyl-
certainly suggest that the antibacterial activity of the complexes dithiocarbazate with 2,5-hexanedione (SMHDH2 and SBHDH2
has been shown by the nature of the constituent compounds.39 respectively) (Scheme 7) have been characterized using various
N,N-Bis(4-nitrobenzaldehyde)ethylenediamine (L1) and N,N- physicochemical and spectroscopic procedures. SBs and their
bis(acetophenone)ethylenediamine (L2) (Scheme 6) and its complexes were evaluated for their ability to hinder the growth

Scheme 5 Structures of the ligands and the formation of complexes 1–3.

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23297
 View Article Online

RSC Advances Review

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Scheme 6 Structures of SBs (L1 and L2).

Scheme 7 Synthesis of the copper complexes from bis(dithiocarbazate) ligands. Reagents and conditions: (a) CS2, KOH, EtOH, 0  C, 1 h; (b) CH3I
or PhCH2Cl, EtOH, 0  C, 5 h; (c) for SMHDH2 (2,5-hexanedione, EtOH, 79  C, 1 h), for SBHDH2 (2,5-hexaedione, EtOH, 79  C, 5 min) and (d) for
CuSMHD [Cu(OAC)2$H2O, MeOH, 65  C, 1 h], for CuSBHD [Cu(OAc)2, acetonitrile, r.t, 1 h].

of ten strains of Gram-negative and Gram-positive bacteria. observation that the SB prepared from 2-benzoylpyridine with S-
Besides that, antiproliferation activity was found to be improved methyldithiocarbazate (SMDTC) was a highly effective inhibitor
by complexation with Cu2+ ions. Moreover, initial screening of E. coli and S. aureus whereas that prepared with the S-ben-
showed copper complexes are powerfully active against human zyldithiocarbazate (SBDTC) analog showed no activity.41
breast adenocarcinoma cancer cell lines MDA-MB-231 and Creaven et al.42 have reported the preparation and screening
MCF-7. In addition, SMHDH2 exhibited a broad range of of linezolid-like SBs as inhibitors of biolm formation. These
moderate activity against various strains. It was most effective compounds in the presence the 2-chloroquinolinyl and 2-
against E. coli AcrAB-, Acinetobacter baumannii, Pseudomonas chloro-8-methylquinolinyl motif, respectively, displayed anti-
aeruginosa and S. aureus, thus making it a potential antimi- bacterial activity superior to that of linezolid and were stronger
crobial agent in the presence of polymyxin B nonapeptide when compared with ciprooxacin. Cu(II) complexes of Schiff
(PMBN). Moreover, the enhanced activity observed for SMHDH2 base-derived coumarin ligands (Fig. 1) have shown good anti-
compared to its S-benzyl analog is consistent with the Candida activity. Moreover, the more active complexes and their

23298 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

agent and also an important antioxidant chemical.45,46 Their

role in the removal of toxic chemicals from biological systems is
excellent. The current literature search has highlighted anti-
bacterial resistance in community pathogens as a major
problem, and to overcome this a new generation of antibiotics
should be revived.47,48 For instance, Shanty et al. have prepared
Schiff bases (H1–H7) (Scheme 9). These compounds were
screened for enzyme inhibition, antibacterial, cytotoxic and in
vivo antidiabetic activities and compounds were found to be
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

active against one or other activity. The ndings indicated that

Zn(II) complexes are a good inhibitor of alkaline phosphatase
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Fig. 1 Structures of Schiff bases 1a–1k and their corresponding enzyme and possess the highest potential against diabetes,
secondary amines 3a–3k showing the numbering system used in the blood cholesterol levels and cancer cells. In other words, the
assignment of 1H and 13C NMR spectra.
difference in the effectiveness of SBs against different organ-
isms depends either on the differences in the ribosomes of
microbial cells or the impermeability of the cells of the
corresponding ligands were investigated in the presence of microbes. Besides that, the inhibition of microbial growth was
Cu(II) in liquid and frozen solution by ESR spectroscopic not observed with the E. coli, possibly due to the presence of an
methods. However, cytotoxicity investigations of the amines, outer protective layer called lipopolysaccharide.49 On the other
together with the Cu(II) complexes and their corresponding hand, some SBs have been prepared by the condensation of 2-
ligands, against human colon cancer and human breast cancer aminophenol, 2-amino-4-nitrophenol, 2-amino-4-
cells recognized the chemotherapeutic potential of SBs.43,44 methylphenol, and 2-aminobenzimidazole with thiophene-2-
On the other hand, new compounds from SBs were prepared carboxaldehyde and pyrrole-2-carboxaldehyde. SBs individu-
by the reaction of salicylaldehyde with semiaromatic diamines ally exhibited varying degrees of inhibitory effects on the growth
which were synthesized by the reduction of the corresponding of the tested bacterial species. Form these works, compounds
dinitro groups. For SB ligands (Scheme 8), their precursors and containing electron-donating groups (OH) show moderate
metal complexes were also examined for antibacterial, anti- activity against the bacteria Salmonella Typhi, Bacillus coagu-
tumor, brine shrimp lethality, antifungal, DPPH free-radical lans, Bacillus pumills, Clostridium and good activity against
scavenging and DNA damage assays. The data of these anal- Bacillus circulans. Moreover, SBs containing electron-acceptor
yses showed the essential potential of the prepared SBs, their groups (NO2) did not exhibit any signicant effect against the
precursors and copper(II) complexes in the biological eld as same bacterial strains.50
near future drugs.45 As in other modied isatin compounds, SBs have been
2.1.2 Heterocyclic Schiff bases. SBs containing heterocyclic synthesized by reacting 5-substituted isatins with bioactive
moieties deserve special attention because of their signicant compounds from amines or hydrazides. This work examined
role in biological processes as a very good chemotherapeutic the effect of isatin N-substitution on the bioactivity of the
resulting SBs (Scheme 10). Compounds containing functional
groups CH3 (2d), F (3b), Cl (5c) and CH3 (6d) were among the
most potent derivatives against P. aeruginosa (MIC (minimum
inhibitory concentration) ¼ 6.25 mg mL1). This is an impor-
tant result since P. aeruginosa is a highly opportunistic path-
ogen and SBs with activity against this pathogenic bacterium are
of singular assessment. Analysis of the structure–activity rela-
tionship showed that the incorporation of (SH) urea-based
Schiff bases leads to stronger derivatives with a broader spec-
trum of antibacterial activity. In addition, highly lipophilic
compounds such as 11a–12c did not show any measurable
antibacterial activity, which suggests that an optimal lip-
ophilicity might be an important requirement for the antibac-
terial activity of the studied isatins.51
Khan et al.52 have reported the synthesis and evaluation for
in vitro antiglycation of bis-Schiff bases (Scheme 11). Some of
these bis-Schiff bases such as compounds 1 (IC50 (degree of
antiglycation activity) ¼ 291.14  2.53 IM), 2 (IC50 ¼ 257.61 
5.63 IM), and 3 (IC50 ¼ 243.95  4.59 IM) showed an admirable
antiglycation activity, better than the normal (rutin, IC50 ¼
294.46  1.50 IM). A remarkable effect on the antiglycation
Scheme 8 Synthesis of SB ligands. activity was exhibited owing to the presence of electron-

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23299
 View Article Online

RSC Advances Review

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Scheme 9 Preparation of Schiff bases (SBs).

withdrawing groups at isatin. Therefore, this difference in ethyl-2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-

activity might be due to the presence of the Cl group. 1,2,4-triazole-1-yl) acetate (2), obtained in basic medium from 4-
Moreover, a series of new pyrazole-based SBs (Scheme 12) were amino-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-one (1).
synthesized and characterized by spectral analyses. Prepared Compound 3 was converted to the thiosemicarbazide and SB
compounds were evaluated for their antibacterial activity against derivatives (Scheme 13). As with results for bioactivity, the
Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa, thiosemicarbazide derivatives also exhibited antibacterial
and Escherichia coli. As a result, compound 3f was shown to have activity against Bacillus cereus, Staphylococcus aureus, and
admirable activity against S. aureus compared with a standard Mycobacterium smegmatis. Moreover, the thiosemicarbazide
against the remaining three microorganisms.53 group deserves deliberation in the synthesis of bioactive Schiff
In this same review, essential compound 2-(4-amino-5-oxo-3- bases. The reason for Gram () bacteria [Escherichia coli,
(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1-yl) acetohy- Yersinia pseudotuberculosis, and Pseudomonas auroginosa]
drazide (3) was prepared by reacting hydrazine hydrate with being resistant to the compounds tested may be due to the

23300 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Scheme 10 (I) Synthesis route to Schiff bases of 5-substituted isatins. (II) Synthetic routes to compound 7 and Schiff bases of N-arylmethylisatin
11a–13c. Reagents and conditions: (a) phenylhydrazine, ethanol 96% (w/w), acetic acid; (b) fluorinated benzyl chlorides, K2CO3, KI, acetonitrile;
(c) compounds 8–10, ethanol 96% (w/w), acetic acid.

relatively more important structure of the cell wall including complexes were screened for their biological activity against
the more closely spaced peptidoglycan and extra lipopolysac- bacterial species, two Gram-positive bacteria (B. subtilis and
charide layers.54 S. aureus) and two Gram-negative bacteria (E. coli and P. aer-
In continuation of these elds on Schiff bases and their uginosa). In addition, the inuence of the metal ion of the
complexes, several works have been reported on the synthesis complexes upon the antibacterial activity against the tested
and characterization of Schiff base ligands and their complexes: Gram-positive and -negative organisms shows that the
3-amino-4-{1,5-dimethyl-3-[2-(5-methyl-1H-indol-3-yl)-ethylimino]- complexes have an enhanced activity compared to the ligand
2-phenyl-2,3-dihydro-1H-pyrazol-4-ylazo}phenol54 and 3-[2-(1H- itself. Such increased activity of the complexes can be
indol-3-yl)-ethylimino]-1,5-dimethyl-2-phenyl-2,3-dihydro-1H- explained on the basis of Tweedy’s chelation theory.58 Chela-
pyrazol-4-ylamine, 1-{[2-(1H-indol-3-yl)-ethylimino] methyl} tion reduces the polarity of the metal ion considerably because
naphthalene-2-ol and dicyclohexyl amine and 4-((2-hydroxy-1- of the partial sharing of its positive charge with the donor
naphthyl)methylene amino)-1,5-dimethyl-2-phenyl-1H-pyrazol- group and also due to p-electron delocalization on the whole
3(2H)-one (HL).55–57 The previous ligands and their metal chelate ring.

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23301
 View Article Online

RSC Advances Review

pharmacophore for drug design.60–63 For instance, three

ferrocene-based SB Cu(II) complexes, i.e. bis(N-(2-hydroxy-
benzylidene)-4-ferrocenylaniline) copper(II) (Cu(L1)2), bis(N-
(2,3-dihydroxybenzylidene)-4-ferrocenylaniline) copper(II) (Cu(L2)2),
and bis(N-(5-chloro-2-hydroxybenzylidene)-4-ferrocenylaniline)
copper(II) (Cu(L3)2) (Scheme 14), were prepared from ferrocenyl
SBs. The synthesized SBs and their Cu(II) complexes were
characterized by various spectroscopic and electroanalytical
methods. Moreover, the SBs exhibited signicant activity in
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

brine shrimp cytotoxicity and antitumor assays with IC50 values

ranging from 2.32 to 69.61 mg ml1. Also, the SB complexes were
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

found to be more active than their ligands with lower IC50 values.
A DNA–drug interaction study through voltammetry revealed
their binding nature which complemented the antitumor
behaviour evaluated from biological studies.64 This interaction is
logically acceptable due to the presence of Fe2+ in the form of the
ferrocene moiety in the solution of compound which can
Scheme 11 Synthesis of bis-Schiff from isatins.
interact with the negatively charged phosphate groups of DNA.
Zaheer et al.65 have reported the synthesis of ferrocene SBs
2.1.3 Ferrocene-based Schiff bases. Ferrocene-based (1–5) by the condensation of 4-ferrocenyl aniline with different
organometallics and metal complexes possess unique proper- substituted aromatic aldehydes and acetyl acetone (Scheme 15).
ties like stability, aromaticity, redox activity, lipophilicity and These compounds showed low cytoxicity and appreciable anti-
different membrane permeation. Ferrocene containing metal– fungal, antioxidant and DNA-protection activities due to the low
ligand complexes can be regarded as multinuclear molecules solubility of Schiff bases in DMSO.
possessing the features of both coordination chemistry and of 2.1.4 C6-Schiff bases. To further enhance the antimicrobial
organometallics.59 Moreover, ferrocenyl Schiff bases derived activities of chitosan, three types of different C6-Schiff base
from aryl amines and their complexes show potent antitumor derivatives (Scheme 16) of chitosan have been synthesized in
and DNA-protecting activity due to their interesting electro- the deprotection of C2–NH2 with cation exchange resin. There-
chemical properties, thus making them an attractive fore, the antibacterial activities of the compounds were tested in

Scheme 12 Synthetic route for SBs.

23302 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Scheme 13 Synthetic pathway for the protection of target compounds 2, 3, 4, 5, 6 and 7.

the research, and experimental data exhibited that the chitosan another work has been published on the gra copolymerization
derivatives had considerably improved antibacterial activity; of chitosan with acrylonitrile prepared by free radical poly-
therefore, the results indicated that the antimicrobial activity of merization using potassium persulfate (K2S2O8) as the initiator
the SBs was stronger than that of chitosan and was dependent (Scheme 18). The results of antibacterial activity of the original
on the substituent groups (Scheme 17). On the other hand, chitosan exhibited that the antimicrobial activity increased with

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23303
 View Article Online

RSC Advances Review

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Scheme 14 Synthesis of copper complexes [Cu(L1)2–Cu(L3)2].

Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

the increase in percentage graing, so the modied SB was

carried out on the highly graed Ch-g-PAN at 155%. This was
due to the interaction between the positively charged chitosan
molecules and the negatively charged microbial cell membrane.
The interaction was mediated by electrostatic forces between
the protonated –NH+ groups of chitosan and the electronegative
charge on the microbial cell surface.66–68
Some attempts to develop a new category of medical candi-
dates with antimicrobial and anticancer efficacy in a series of
SBs bearing salicylidene ionic liquid (IL-Sal) brushes (ILCSB1-3,
poly-(GlcNHAc-GlcNH2-(GlcN-Sal-IL))) (Scheme 19) was effec-
tively prepared by adopting efficient synthetic paths. In
conclusion, the functionalization of chitosan with IL-Sal
brushes together with metalation of the formed ILCSBs syner- Scheme 16 Synthesis of C6-Schiff bases of chitosan derivatives.
gistically improved its antimicrobial and antitumor features to
a great extent.69

2.2. Schiff bases as corrosion inhibitors

Schiff bases used as inhibitors may block anodic, cathodic or
both sites, thus preventing the metallic substrate from under-
going hydrogen evolution reactions or metal dissolution with
a predominance of lm-developing surface adsorption. The
corrosion inhibition efficiency of organic inhibitors has been
reported to be shown by a strong affinity for inorganic surfaces,
with low inuences on the atmosphere.70 They build up
protective hydrophobic lm molecules adsorbed on the metallic
surface, thus providing a barrier to the dissolution of the
substrate in the electrolyte. The inhibitory action of SBs has
been described by a well-recognized model,71–73 which involves
the adsorption of SBs on the corroding metal surface with
Scheme 17 Synthesis of chitosan Schiff bases (ChBs).
displacement of adsorbed water molecules from the metal
surface as represented by the following eqn (1):

Scheme 15 Synthesis of Schiff bases 1–5.

23304 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

inhibition performance due to the decreasing solubility in

aqueous solution. The inhibition performance could be
improved if the hydrogen atom attached to the carbon in the
ring is replaced by electron-donating substituents such as
–CHO, –NH2, or –CO2H.78 This will lead to changes in electron
density in the metal at the point of attachment, resulting in
retardation of the cathodic or anodic reaction, thereby mini-
mizing corrosion. Here, we focused on anti-corrosion of some
metals such as mild steel and aluminium using Schiff bases.
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Details on these metals are given below.

2.2.1 Mild steel. Some works have reported the protective
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

evaluation of four Schiff bases, namely N1,N10 -(1,4-phenylene)

bis(N4-(4-nitrobenzylidene)benzene-1,4-diamine) SB-I, N,N0 -
(1,4-phenylene)bis(N-benzylidenebenzene-1,4-diamine) SB-II,
N,N0 -(1,4-phenylene)bis(N4-(4-methylbenzylidene)benzene-1,4-
diamine) SB-III, and N1,N10 -(1,4-phenylene)bis(N4-(4-methoxy-
benzylidene)benzene-1,4-diamine) SB-IV (Scheme 20) for mild
steel in 1 M HCl. The corrosion efficiency of SBs for mild steel is
71.42%, 89.52%, 92.85% and 96.19% for SB-IV, SB-I, SB-II and
Scheme 18 Modification of chitosan-graft-polyacrylonitrile. SB-III, respectively. Electrochemical analysis revealed that all of
the SBs behaved as mixed-type inhibitors but predominantly of
a cathodic type.79 The presence of the inhibitor causes
SB(sol) + aH2O(ads) 4 Org(ads) + aH2O(sol) (1) a decrease in the corrosion current (icorr). The highest reduction
in icorr was obtained for SB-IV. This decrease in corrosion
The four main modes of adsorption associated with inhibitor current is due to the increase in blocked fraction of a metal
organic molecules at metal surfaces include (I) electrostatic surface by physical adsorption and the order of inhibition effi-
interaction of the corrosion inhibitor (CI) with the metal ciency is a follows: SB-IV > SB-III > SB-II > SB-I.
surface, (II) charge sharing between the metal and the CI, p- Another study investigated the effect of three SBs, namely,
back bonding, and organometallic complex formation.74 1,3-bis[2-(2-hydroxybenzylidenamino)phenoxy]propane (P1),
Furthermore, (III) the stability of the adsorbed organic molecule 1,3-bis[2-(5-chloro-2-hydroxybenzylidenamino)phenoxy]propane
lms/layer on the substrate surface depends on the nature of (P2), and 1,3-bis[2-(5-bromo-2-hydroxybenzylidenamino)phenoxy]-
the functional groups, possible steric factors, aromaticity, propane (P3) (Fig. 2), on the anti-corrosion of mild steel using
electron density of the donor atoms, the type of corrosive electrochemical tests. Polarization measurements suggest that P1
solution and nature of the interaction between its (IV) p-orbital acts as mixed-type inhibitor (synergistic effect) whereas P2 and P3
with the d-orbital of the metal. The inhibitory efficiency of these behave as mainly cathodic inhibitors for the acidic corrosion of
SBs is related to the structural nature of the SBs with N, S, O and steel. Electrochemical measurements show that inhibition effi-
P heteroatoms in the molecules, which serve as reaction cores ciencies increase with an increase in the concentration of the
for physical adsorption on the substrate surface.75 The inhibi- organic compound. This reveals that the inhibitive actions of SBs
tion efficiency of the heteroatoms in SBs follows the sequence O were mainly due to adsorption on the metal surface. Adsorption of
< N < S < P.76,77 The transfer of electrons from these compounds these organic compounds follows the Temkin adsorption
to the substrate surface is facilitated by the availability of lone isotherm. On the other hand, the results indicate that P2 and P3
pairs and p-electrons in the organic molecules, leading to are shied to a negative direction; this effect is more evident at
formation of coordinate covalent or non-covalent bonds with higher concentrations.80 The difference in protection activities of
the metals. The strength of the physical bond, and thus the the reported inhibitors could be assigned to the presence of the
performance of the SBs depend on the electric charge density on electron-donating groups such as Br or Cl. These data show that
the donor atom of the functional group, the polarizability of the the presence of Cl and Br atoms on the aromatic ring in P2 and P3
group and the electronic and stereo structure of the organic decreases the electronic density on the imine (C]N) group,
molecules. The inhibition action could be due to the adsorption oxygen and also the aromatic ring, which are responsible for
of the organic molecules or its ions on anodic and/or cathodic adsorption on the metal surface. On the other hand, some authors
sites, an increase in the cathodic and/or anodic overpotential, have reported the investigation of triazole SBs (3-bromo-4-uoro-
and the ability to form a protective barrier lm. Some of the benzylidene)-[1,2,4]triazol-4-yl-amine (BFBT), (4-triuoromethyl-
issues that could inuence inhibition action include the chain benzylidene)-[1,2,4]triazol-4-yl-amine (TMBT) and (2-uoro-4-
molecular/length size, bond strength, conjugated/aromaticity nitro-benzylidene)-[1,2,4]triazol-4-yl-amine (FNBT) (Fig. 3) as
bonding, number and type of bonding atoms in the molecule, corrosion inhibitors on mild steel in 0.5 M HCl by chemical and
cross-linking ability and solubility in the environment. electrochemical techniques. They found that the change in Ecorr is
However, with increasing chain length of the hydrocarbon, less than 85 mV, so the studied inhibitors are neither anodic nor
there is a tendency to observe a diminishing in the corrosion cathodic but of the mixed type. This means that even though the

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23305
 View Article Online

RSC Advances Review

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Scheme 19 Schematic representation of ionic liquid-anchored chitosan Schiff bases and their metal complexes.

kinetics of both metal dissolution and hydrogen evolution are dissolution and cathodic hydrogen evolution mechanism are
altered by the addition of SBs, the one which is going to be more affected in the presence of the inhibitor.82
affected is the reduction of iron.81 The studied SBs were 2-((1E)-2-aza-2-pyrimidine-2-ylvinyl)
Schiff bases (Fig. 4) derived from heterocyclic amines and thiophene, 2-((1Z)-1-aza-2-(2-pyridyl)vinyl)pyrimidine (PT), 2-
aldehydes have been prepared and evaluated as organic inhib- ((1E)-2-aza-2-(1,3-thiazol-2-yl)vinyl)thiophene, and 2-((1Z)-1-aza-
itors for metal in 1 M H2SO4 by electrochemical measurements. 2-(2-thienyl)vinyl)benzothiazole (PP) (Fig. 5). Electrochemical
In addition, the corrosion current density (icorr) values decrease results indicated that SBs act essentially as an anodic inhibitor.
with an increase in SB concentration suggesting the effective- The difference in inhibitive efficiency of the organic inhibitor
ness of SBs as organic inhibitors, therefore, Ecorr values are mainly depends on the type and nature of heteroaromatic rings
slightly shied towards the negative direction and the Tafel present in the chemical molecule. As a result from this work, the
constants ba and bc are changed with an increase in concen- difference in inhibition efficiency between PT and PP arising
tration of the inhibitor, suggesting that both the anodic due to the presence of the p electron excess ring (i.e. thiophene)

23306 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Scheme 20 Synthetic route for the preparation of SBs.

3,5-diyl)dimethanol (DMATD) (Fig. 8) for metal corrosion in HCl

have been examined by electrochemical, spectroscopic and
computational studies. The results showed that these synthesized
compounds act as effective inhibitors for mild steel in HCl. The
inhibition efficiency of these organic compounds increases with
their concentration on the metal surface, whereas it decreases with
temperature and HCl concentration. The corrosion measurement
values indicate that in the presence of inhibitors, the displacement
in the value is <85 mV when compared to that of the blank solution,
which proposes a mixed type behavior for SBs.87
El-Lateef et al.88 have reported synthesis and characterization
Fig. 2 Molecular structure of investigated SBs (P1: X ¼ H; P2: X ¼ Cl; three SB compounds (Scheme 21) by X-ray, 13C-NMR, 1H-NMR,
P3: X ¼ Br). mass, UV-vis, FT-IR, spectral data, and elemental analyses.
Moreover, the corrosion inhibition of the studied inhibitors
towards carbon steel in 15% HCl was examined by using elec-
in PT instead of the presence of the p electron decient ring (i.e. trochemical measurements, SEM, and EDX. The result in this
pyridine) PP as a substituent. In this regard, the presence of the work conrmed that the formation of the adsorbed layer of SBs
releasing p electron excess ring in PT causes an increase in the provided the protective property against corrosion, resulting in
electron density of the imine groups (CH]N) in the chemical excellent corrosion inhibition. Therefore, the presence of HA-3
structure which offers a better protective action of the metal as an organic inhibitor results in a comparatively cleaner and
than PP.83 In addition, the inhibition effect of SBs (Fig. 6 and 7) smoother surface. This nding elucidates a good physical
on the corrosion of metal in 1 M HCl has been investigated by adsorption and corrosion inhibition potentiality of HA-3
polarization and electrochemical impedance spectroscopy. The compared to HA-1.
polarization curve results revealed that SBs act as mixed type SBs, namely 2-amino-6(2-hydroxybenzelideneamino)hexanoic
(cathodic/anodic) inhibitors.84–86 acid (SB-1), 2-amino-6-(4-methoxybenzelideneamino)hexanoic
Three triazole Schiff bases, namely (4-(4-hydroxybenzyl- acid (SB-2) and 2-amino-6-(4-dimethylamino)benzyli-deneamino)
ideneamino)-4H-1,2,4-triazole-3,5-diyl)dimethanol (HATD), (4- hexanoic acid (SB-3) (Scheme 22), derived from lysine and three
(4-methoxybenzylideneamino)-4H-1,2,4-triazole-3,5-diyl)dimethanol different aldehydes were prepared and evaluated as organic
(MATD) and (4-(3,4-dimethoxybenzylideneamino)-4H-1,2,4-triazole- inhibitors for metals in HCl solution using electrochemical

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23307
 View Article Online

RSC Advances Review

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Fig. 3 Optimized geometrical configurations of BFBT, TMBT, and FNBT.

addition, some researchers have studied the effect of SBs

derived from L-tryptophan, methyl 2-((2-hydroxybenzylidene)
amino)-3-(1H indol-3-yl)propanoate (S1) and 2-(((1-hydroxy-3-
(1H-indol-3-yl)-1,1-diphenylpropan-2-yl)imino)methyl)phenol (S2)
(Scheme 23), on the corrosion performance of stainless steel was
examined. They found that the inhibitors S1 and S2 have good
inhibition efficiency on the corrosion of metals in HCl solution.
Fig. 4 (((5-Phenyl-1,3,4-thiadiazol-2-yl)imino)quinolone-2-ol/thiol). Polarization tests conrmed a mixed mode of inhibition of S1
and S2 with predominant control of the cathodic reaction.90
Gupta et al. have reported the synthesis and characterization
methods. The data showed that the inhibition efficiency increases of SBs by elemental analyses, electronic, IR and NMR spectral
with the increasing concentration of the SBs. Electrochemical studies. In this study the structures of the SBs (Scheme 24) were
measurements revealed that the studied SBs act as cathodic- stabilized by intermolecular H-bonding. On the other hand, the
type inhibitors. It is shown that the addition of SBs retards electrochemical performance of the SBs exhibits quasi-
both cathodic and anodic reactions; however, the cathodic reversible one-electron redox behaviour. Moreover, the corro-
reactions are comparatively more affected than the anodic sion inhibition studies of SBs have been carried out by using
reactions, suggesting that the investigated SBs are mixed-type potentiodynamic polarization and electrochemical impedance
inhibitors and act predominantly as cathodic inhibitors.89 In spectroscopy (EIS) tests. Further, the reduction in anodic and

Fig. 5 Structures of studied Schiff bases.

23308 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Fig. 6 Chemical structure of the investigated compounds.

electrochemical performance of these SBs was investigated on

a metal surface in 1 M HCl solution, and was tested using
potentiodynamic polarization (PDP) and electrochemical
impedance spectroscopy (EIS). The results of the electro-
chemical procedures showed that the studied molecules
imparted high resistance in allowing the ow of electrons
across the metal–electrolyte platform and behaved as mixed-
type inhibitors, with 4 EMP showing better inhibition proper-
ties than 4 NMP.92
Schiff base compounds (Z)-N-(2-chlorobenzylidene)naphthalen-
1-amine (CBN) and (Z)-N-(3-nitrobenzylidene)naphthalen-1-amine
(NBN) (Scheme 26) have been prepared by the reaction of 1-
naphthylamine and 2-chlorobenzaldehyde or 3-nitrobenzaldehyde
respectively. The structures of the compounds were further veried
using density functional theory (DFT) which showed the role of the
electrons towards corrosion inhibition. Electrochemical measure-
Fig. 7 Chemical structure of the tested SBs. ments using potentiodynamic polarization and electrochemical

Fig. 8 Structure of inhibitor molecule.

cathodic current densities at a given applied potential shows

that these SBs inhibit the reduction of hydrogen ion as well as
dissolution of the metal.91 On the other hand, 4-(((4-ethyl-
phenyl)imino)methyl)phenol (4 EMP) and (E)-4-((naphthalen-2-
ylimino)methyl)phenol (4 NMP) (Scheme 25) have been
prepared by the reaction of 4-hydroxybenzaldehyde with 4-eth- Scheme 21 Representation procedures for the synthesis of Schiff base
ylaniline (for 4 EMP), or naphthalene-2-amine (for 4 NMP). The compounds.

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23309
 View Article Online

RSC Advances Review

Scheme 22 Synthetic route for investigated SBs.

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

dissolution is more pronounced than that on the cathodic

reduction, and IM can be characterized as an anodic inhib-
itor.96,97 Therefore, the corrosion inhibition and adsorption of
N,N0 -bis(n-hydroxybenzaldehyde)-1,3-propandiimine (n-HBP)
(Fig. 9) SBs have been investigated on steel electrode in 1 M HCl
by using electrochemical techniques. Therefore, the results
propose that the highest inhibition efficiency was obtained for
3-HBP. Polarization curves reveal that all studied inhibitors are
of mixed type.98
The corrosion inhibition effect of o-aminophenol-N-benzyli-
Scheme 23 Chemical structure of Schiff base molecules S1 and S2. dene (o-AmphNB) and o-anisidene-N-benzylidene (o-AnsNB)
(Fig. 10) for aluminium in 1 M HCl at different concentrations of
the two different SBs has been studied by means of potentiody-
namic polarization and electrochemical impedance spectroscopy
(EIS). In this work, potentiodynamic polarization parameters
exhibited the mixed mode of inhibition with predominance of
cathodic inhibition. The impedance results revealed that with
a rise in the concentration of the inhibitor, the charge transfer
resistance increases while the double layer capacitance
decreases.99 On the other hand, the corrosion inhibition effi-
ciency of 2-((pyridin-2-ylimino)methyl)phenol (S1), 2-((hexa-
decylimino)methyl)phenol (S2), 2-((4-hydroxyphenylimino)methyl)
phenol (S3), and 1-(4-(2-hydroxybenzylideneamino)phenyl)etha-
none (S4) for carbon steel in 1 M HCl has been studied. Polar-
ization and electrochemical impedance spectroscopy
experiments showed that SBs are the best used inhibitor. The
results of electrochemical impedance and Tafel polarization
Scheme 24 Synthesis of ferrocene carboxaldehyde propanoylhy- measurements consistently showed that, all compounds are
drazone (fcph) and ferrocene carboxaldehyde furoylhydrazone (fcfh) good inhibitors. Polarization curves indicated that the studied
Schiff bases. SBs acted as mixed (cathodic/anodic) inhibitors. The differ-
ences in the corrosion inhibition efficiency between four
studied SBs are correlated with their chemical structures.100
impedance spectroscopy revealed that both compounds are very SB derivatives, namely N0 -(4-hydroxybezylidene)nicotinic
good corrosion inhibitors, with CBN showing better properties. hydrazone (HBNH) and N0 -(4-methylybezylidene)nicotinic hydra-
Therefore, an increase in the SB concentration with inhibition zone (MBNH) (Fig. 11), have been studied as organic inhibitors for
efficiency is accompanied by a decrease in Icorr.93–95 In addition, iron in 1 M HCl using electrochemical methods. The results show
a Schiff base (N-isonicotinamido-3-methoxy-4-hydroxybenzalal- good corrosion inhibition efficiency, with the inhibition efficiency
dimine, IM) compound (Scheme 27) based on the avoring of MBNH being higher than that of HBNH. This can be explained
(vanillin) and medicine (isoniazid) has been prepared and through the protonation of the hydroxyl group in 1 M HCl solution
utilized as a green corrosion inhibitor for copper in aggressive decreasing the p-electron density in the aromatic ring of HBNH
media. Electrochemical techniques are carried out to analyze which causes a weaker physical interaction between the metal
its inhibition property. However, the current density of the surface and HBNH molecules as compared to that in case of
cathodic part changes slightly compared to that of the blank MBNH. Moreover, both compounds can be classied as mixed-
plot. Therefore, the Ecorr value of the Cu electrode shis to type inhibitors with a predominant in cathodic effect.101
positive aer the addition of the inhibitor. These phenomena Two SBs, 5-bromo-2-[(E)-(pyridin-3-ylimino)methyl]phenol
reveal that the inuence of the inhibitor on the anodic metal (HBSAP) and 5-bromo-2-[(E)-(quinolin-8-ylimino)methyl]phenol

23310 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Scheme 25 Reaction pathway showing the formation (E)-4-((naphthalen-2-ylimino)methyl)phenol Schiff base.

Scheme 26 Reaction route for the preparation of (a) (Z)-N-(2-chlorobenzyllidene)naphthalene-1-amine, and (b) (Z)-N-(3-nitrobenzyllidene)
naphthalene-1-amine.

(HBSAQ) (Fig. 12) have been prepared. The inhibition activity of and conjugated ring in the structure of these SBs. Omanovic and
these SBs for metal in aggressive solution with 0.1 M HCl for both Metikos-Hukovic103 stated that the stereo size of the adsorbed
short and long immersion times was investigated using electro- molecules inuences the inhibitory properties of SBs.
chemistry and surface characterization. Potentiodynamic polari- Behpour et al.104 have investigated the inhibiting action
zation revealed that the organic molecule is more adsorbed on of SBs, namely SB1: 2-({-1-methyl-3-[(2-sulfanylphenyl)imino]
the cathodic sites. Therefore, its corrosion efficiency increases butylidene}amino)-1-benzenethiol and SB2: 2-({-1,2-diphenyl-2-
with increasing organic inhibitor concentration.102 In addition, [(2-sulfanylphenyl)imino]ethylidene}amino)-1-benzenethiol
the higher values of inhibition efficiencies were possibly due to (Fig. 13) on the corrosion of metal in HCl. The SBs were
the presence of the imine group and conjugated and aromatic prepared and examined as organic inhibitors for the corrosion
molecules. As a result, the sequence of inhibition efficiency found of Cu metal. Electrochemical measurements consistently iden-
from the electrochemical measurements to be as follows: HBSAQ tify both compounds as good organic inhibitors. Therefore,
> HBSAP. The higher inhibition efficiency of organic inhibitor impedance spectroscopy (EIS) discovered that the corrosion of
HBSAQ may be assigned to the presence of one more aromatic Cu in HCl was inuenced to some extent by mass transport

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23311
 View Article Online

RSC Advances Review

Scheme 27 Reaction of vanillin with isoniazid.

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

since the Warburg impedance was shown in some circum-

stances. Moreover, polarization curves reveal that both of the
studied SBs act as mixed type (cathodic/anodic) inhibitors.
Differences in inhibition efficiency between SB1 and SB2 are
associated with their chemical and stereo structures.
Other works105 have reported the inhibition effect of three
SBs (SB-I, SB-II and SB-III) (Fig. 14) and their synergistic effect
with KI on the corrosion of iron in acidic solution by electro-
chemical measurements such as potentiodynamic polarization

Fig. 9 Chemical structures of the Schiff bases.

Fig. 11 Chemical structure of the synthesized corrosion inhibitors: (a)

N0 -(4-hydroxybezylidene)nicotinic hydrazone (HBNH), and (b) N0 -(4-
methylbezylidene)nicotinic hydrazone (MBNH).

Fig. 10 Chemical structures of the synthesized inhibitors. Fig. 12 Chemical structures of the synthesized SBs.

23312 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Fig. 14 Chemical structure of SBs.

3-oxopentane (D1), 1,5-bis[2-(5-chloro-2-hydroxybenzylidene-

amino)phenoxy]-3-oxopentane (D2) and 1,5-bis[2-(5-bromo-2-
Fig. 13 Structure of the investigated SBs. hydroxybenzylideneamino)phenoxy]-3-oxopentane (D3) (Fig. 17)
and their inhibitive capabilities on the corrosion of aluminium
in acidic solution. Electrochemical measurement curves
and electrochemical impedance spectroscopy. Scanning elec- demonstrated that the studied SBs were a cathodic inhibitor and
tron microscopy (SEM) was used to characterize the steel the effectiveness of these inhibitors decreased in the order of D3
surface. The inhibition efficiency increases with the concen- > D2 > D1. It means that Br-substituted SB has a more protective
tration of the Schiff bases and increases further with the pres- ability than the Cl-substituted one, and Cl-substituted SB is
ence of KI. The thermodynamic parameters Kads and DGads are more protective compared to its unsubstituted derivative.
calculated and discussed. The probable inhibitive mechanism Similar results were documented by previous work111 where
is proposed from the viewpoint of adsorption theory. According bromine including a phenolic SB is a more effective inhibitor
to the results in this work, the Icorr value decreases substantially, than its Cl-substituted and unsubstituted derivatives.
leading to higher inhibition efficiency of the KI/SB (SB-I, SB-II Other works investigated the effect of Schiff bases containing
and SB-III) mixtures, up to 98.6%, 98.9% and 99.4%, aza groups such as 2-[2-aza-2-(5-methyl(2-pyridyl))vinyl]phenol,
compared to 57.6%, 84.7% and 89.5% obtained for 0.0005 M of 2-[2-aza-2-(5-methyl(2-pyridyl))vinyl]-4-bromophenol, 2-[2-aza-2-
SB-I, SB-II and SB-III alone, respectively. This reveals a syner- (5-methyl(2-pyridyl))vinyl]-4-chlorophenol (Fig. 18) on the
gistic effect among SBs and KI.106,107 corrosion behaviour of aluminum in 0.1 M HCl, studied using
The inhibition effect of SBs (Fig. 15) on the corrosion of iron electrochemical methods. Polarisation curves show that all of
in HCl has been studied by polarization, electrochemical the investigated SBs acted as mixed-type inhibitors. Electro-
impedance spectroscopy (EIS) and weight loss measurements. chemical measurements show that inhibition efficiencies
The results of this work show that all studied SBs act as effective increase with the rise in organic inhibitor concentration. These
organic inhibitors. The corrosion inhibition increases when the results reveal that the inhibitive actions of SBs were due to
concentration of the SBs increases. This study reveals that by physical adsorption on the aluminium surface. As a result, the
increasing the SB concentration, Icorr was decreased, Ecorr was variation in inhibition efficiency values depends on the type of
shied slightly to more positive values, and the inhibition functional groups substituted on the aromatic ring. Therefore,
efficiency IEP (%) increased.108 it was found that the presence of Br and Cl atoms in the
a-Aminophosphonate (a-APD) and SB (E-NDPIMA) deriva- chemical structure of the investigated SBs facilitate the
tives (Fig. 16) have been synthesized and their structures were adsorption of the molecule on the aluminium surface. On the
proved by IR, UV-vis, 1H, 13C and 31P NMR spectroscopy. Their other hand, the adsorption of the investigated SBs depends on
inhibitive capacities on the corrosion of carbon steel in H2SO4 the charge density of the adsorption centers and dipole
solution were ascertained by Tafel polarization and electro- moments.112
chemical impedance spectroscopy (EIS). Experimental results The inhibitory effect of two SBs, and 3-(5-nitro-2-hydroxyl-
claried that the prepared compounds are effective inhibitors benzylideneamino)-2-(5-nitro-2-hydroxyphenyl)-2,3-dihydro-
and the adsorption of organic molecules on the Fe surface obeys quinazoline-4(1H)-one (NNDQ) (Fig. 19), on the corrosion of
the Langmuir adsorption isotherm.109 metal surface in 1 M HCl acid were investigated using poten-
2.2.2 Aluminium. Safak et al.110 have reported the synthesis tiodynamic polarization and electrochemical impedance spec-
of SBs named 1,5-bis[2-(2-hydroxybenzylideneamino)phenoxy]- troscopy measurements. The investigation results reveal that

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23313
 View Article Online

RSC Advances Review

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

Fig. 15 Names and structures of the investigated SBs.

Fig. 16 Synthesis route of the studied compounds: (a) 4-(dimethylamino)benzaldehyde, (b) aniline, (c) (E)-N,N-dimethyl-4-((phenylimino)
methyl)aniline (E-NDPIMA), (d) diethylphosphite, and (e) diethyl ((4-(dimethylamino)phenyl)(phenylamino)methyl)phosphonate (a-APD).

23314 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Fig. 17 General structure of the investigated SBs.

Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

the SB compounds with an average efficiency of 92% at an

additive concentration of 1.0 mM have fairly effective inhibiting
properties for Al metal in HCl, and they show mixed-type
inhibitor character. This phenomenon revealed that the SBs
may suppress both anodic metal dissolution and the cathodic
reaction to produce hydrogen gas with the increase in the SB
concentration. The occurrences of CH]N, the phenolic group
(–OH), and benzene rings are responsible for their greater
activity and inhibition efficiency. The analysis of the results in
Fig. 18 Schiff bases. this work revealed that the presence of weak electron-donating
groups, i.e. methoxy (–OCH3), and the strong deactivating
group, the nitro group (–NO2), are responsible for the strong
interaction of the former inhibitor to the latter one.113
Ashassi-Sorkhabi et al.114 have reported the study of Schiff
bases benzylidene-(2-methoxy-phenyl)-amine (a), (2-methoxy-phenyl)-
(4-methyl-benzylidene)-amine (b), (4-chloro-benzylidene)-(2-methoxy-
phenyl)-amine (c), and (4-nitro-benzylidene)-(2-methoxy-phenyl)-
amine (d) (Fig. 20) on the corrosion of aluminum in 1 M HCl,
by polarization and electrochemical impedance spectroscopy
(EIS). The results reveal that the inhibition efficiency increases
with a decrease in temperature and an increase in the concen-
tration of the Schiff base. The polarization curves show that the
Fig. 19 Structure of the investigated SBs: 3-(5-nitro-2-hydroxybenzyl- SBs used are mixed-type inhibitors. As a result, the performance
ideneamino)-2-(5-nitro-2-hydroxyphenyl)-2,3-dihydroquinazoline- of the organic compounds depends strongly on the type of
4(1H)-one (NNDQ).

Fig. 20 Structure of the studied SBs.

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23315
 View Article Online

RSC Advances Review

functional groups substituted on the conjugated benzene 2 T. T. Tidwell, Angew. Chem., Int. Ed. Engl., 2008, 47, 1016–
ring.115,116 1020.
3 W. A. Zoubi and N. D. Al Mohanna, Spectrochim. Acta, Part A,
2014, 132, 112–117.
3. Conclusion 4 H. Schiff, Justus Liebigs Ann. Chem., 1864, 131(1), 118–119.
Imine compounds are considered as a very signicant category 5 H. Naeimi, Z. S. Nazi, S. M. Amininezhad and
of organic compounds because of their capability to form M. Amouheidari, J. Antibiot., 2013, 66, 687–689.
complexes with metal ions and because of their pharmacolog- 6 M. Hajrezaie, M. Paydar, C. Y. Looi, S. Z. Moghadamtousi,
P. Hassandarvish, M. S. Salga, H. Karimian, K. Shams,
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

ical properties. Imine compounds have been revealed to be

promising leads for the design of more competent antimicro- M. Zahedifard, N. A. Majid, H. M. Ali and M. A. Abdulla,
bial agents. According to the results of researches on the Sci. Rep., 2015, 5, 9097–9104.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

corrosion protection of metals, various chemical structures of 7 T. Mukherjee, J. C. Pessoa, A. Kumar and A. R. Sarkar,
Schiff bases are used for protecting metals from aggressive Dalton Trans., 2013, 42, 2594–2607.
environments. Therefore, the review of organic inhibitors used 8 A. Lehwess-Litzmann, P. Neumann, C. Parthier, S. Lüdtke,
for different metals under various conditions makes it possible R. Golbik, R. Ficner and K. Tittmann, Nat. Chem. Biol.,
to choose a competent and cost-effective organic inhibitor for 2011, 7, 678–684.
a specic environment. However, acidic or Cl-containing envi- 9 P. Adaeo, M. L. Kuznetsov, S. Barroso, A. M. Martins,
ronments are the most aggressive surroundings for metals. The F. Avecilla and J. C. Pessoa, Inorg. Chem., 2012, 51, 11430–
corrosion inhibition performance of organic inhibitors in these 11449.
aggressive surroundings is different. Some of the chemical 10 D. Gong, B. Wang, X. Jia and X. Zhang, Dalton Trans., 2014,
structures protect the surface of the metal through the forma- 43, 4169–4178.
tion of a protective oxide layer and some of them decrease 11 P. Das and W. Linert, Coord. Chem. Rev., 2016, 311, 1–23.
corrosion attack through physical and chemical adsorption and 12 W. A. Zoubi and Y. G. Ko, J. Organomet. Chem., 2016, 822,
formation of a complex layer. According to the results from 173–188.
previous works, an increase in the concentration of organic 13 A. M. Abu-Dief and I. M. A. Mohamed, J. Basic Appl. Sci.,
inhibitor in the bulk of the solution and an increase in the 2015, 4, 119–133.
immersion time result in enhancing the corrosion inhibition 14 C. M. Che, S. C. Chan, H. F. Xiang, M. C. Chan, Y. Liu and
behaviour. Moreover, an increase in the temperature of the Y. Wang, Chem. Commun., 2004, 1484–1485.
adsorption process leads to a decrease in the corrosion inhibi- 15 L. Zhou, C. C. Kwok, G. Cheng, H. Zhang and C. M. Che,
tion efficiency. The other hand of this work was to review the Opt. Lett., 2013, 38, 2373–2375.
molecular structure of various imine inhibitors, which are used 16 T. Sano, Y. Nishio, Y. Hamada, H. Takahashi, T. Usuki and
for the protection of different metals. The molecular structure K. Shibata, J. Mater. Chem., 2000, 10, 157–161.
plays a primary role in its corrosion protection. The presence of 17 S. H. Li, F. R. Chen, Y. F. Zhou, J. N. Wang, H. Zhang and
heteroatoms such as nitrogen, sulfur and oxygen with free J. G. Xu, Chem. Commun., 2009, 4179–4181.
electron pairs, alkyl substituents and aromatic rings in the 18 S. A. Lee, G. R. You, Y. W. Choi, H. Y. Jo, A. R. Kim, I. Noh,
structure of the organic inhibitors play a signicant role in their S. J. Kim, Y. Kim and C. Kim, Dalton Trans., 2014, 43, 6650–
protective behaviors. In this study, therefore, a review of the 6659.
corrosion protection of metals in common environments such 19 A. Ganguly, B. K. Paul, S. Ghosh, S. Kar and N. Guchhait,
as acidic media or aggressive solution for metals has been Analyst, 2013, 138, 6532–6541.
given. 20 C. R. Nayar and R. Ravikumar, J. Coord. Chem., 2014, 67, 1–16.
21 W. A. Zoubi, F. Kandil and M. K. Chebani, Arabian J. Chem.,
2016, 9, 626–632.
Conflicts of interest 22 A. W. Jeevadason, K. K. Murugavel and M. A. Neelakantan,
Renew. Sustain. Energy Rev., 2014, 36, 220–227.
The authors declare no competing nancial interest.
23 P. A. Vigato and S. Tamburini, Coord. Chem. Rev., 2004, 248,
1717–2128.
Acknowledgements 24 R. M. Clarke and T. Storr, Dalton Trans., 2014, 43, 9380–
9391.
This research was supported by the First Research Grant (NRF- 25 M. Kose, G. Ceyhan, M. Tümer, I. Demirtas, I. Gonül and
2017R1C1B5077139) and Human Resource Exchange Program V. McKee, Spectrochim. Acta, Part A, 2015, 137, 477–485.
in Scientic Technology (NRF-2018H1D2A2010032) through the 26 M. Shabbir, Z. Akhter, A. R. Ashraf, M. Bolte, S. Wahid and
National Research Foundation of Korea (NRF) funded by the B. Mirza, Eur. J. Chem., 2017, 8, 46–51.
Ministry of Science and ICT, Republic of Korea. 27 M. Calligaris and L. Randaccio, in Comprehensive Coordination
Chemistry, ed. G. Wilkinson, R. D. Guillard and J. A.
References McCleverty, Pergamon, Oxford, 1987, vol. 2, pp. 715–738.
28 R. Hernandez-Molina and A. Mederos, Acyclic and
1 W. Al Zoubi, Int. J. Org. Chem., 2013, 3, 73–95. Macrocyclic Schiff Base Ligands, in Comprehensive

23316 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018
 View Article Online

Review RSC Advances

Coordination Chemistry II, ed. J. A. McCleverty and T. J. Meyer, 53 S. Malladi, A. M. Isloor, S. Isloor, D. S. Akhila and H.-K. Fun,
Elsevier Pergamon, Oxford, 2004, vol. 1, pp. 411–458. Arabian J. Chem., 2013, 6, 335–340.
29 W. A. Zoubi, A. A. S. Al-Hamdani and M. Kaseem, Appl. 54 Y. Ünver, K. Sancak, F. Çelik, E. Birinci, M. Küçük, S. Soylu
Organomet. Chem., 2016, 30(10), 810–817. and N. A. Burna, Eur. J. Med. Chem., 2014, 84, 639–650.
30 W. A. Zoubi, A. A. S. Ali-Hamdani and M. K. Chebani, Sep. 55 A. A. S. Al-Hamadani and W. A. Zoubi, Spectrochim. Acta,
Sci. Technol., 2017, 52(9), 1052–1069. Part A, 2015, 137, 75–89.
31 W. A. Zoubi, F. Kandil and M. K. Chebani, Arabian J. Chem., 56 W. A. Zoubi, A. A. S. Al-Hamdani, I. P. Widiantara,
2016, 9, 526–531. R. G. Hamoodah and Y. G. Ko, J. Phys. Org. Chem., 2017,
32 Z. H. Chohan and S. Kausar, Chem. Pharm. Bull., 1993, 41, 951. 30, 3737.
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

33 V. P. Petrović, M. N. Živanović, D. Simijonović, J. Đorović, 57 W. Al Zoubi, A. A. S. Al-Hamdani, S. D. Ahmed and Y. G. Ko,

Z. D. Petrović and S. D. Marković, RSC Adv., 2015, 5, J. Phys. Org. Chem., 2018, 31, 3752.
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

86274–86281. 58 S. Gaur and B. Sharma, J. Ind. Chem. Soc., 2003, 8, 841.

34 M. Shabbir, Z. Akhter, H. Ismail and B. Mirza, J. Mol. Struct., 59 A. E. Ghaouth, J. Arul, A. Asselin and N. Benhamou, Mycol.
2017, 1146, 57–61. Res., 1992, 96, 769–779.
35 M. Shabbir, Z. Akhter, I. Ahmad, S. Ahmed, H. Ismail, 60 S. Bautista-Baños, A. N. Hernández-López, M. G. Velázquez-
B. Mirza, V. McKee and M. Bolte, J. Mol. Struct., 2016, del Valle, M. Hernández-López, E. Ait Barka, E. Bospuez-
1116, 84–92. Molina and C. L. Wilson, Crop Protect., 2006, 25, 108–118.
36 M. Shabbir, Z. Akhter, A. R. Ashraf, H. Ismail, A. Habib and 61 S. Bautista-Baños, M. Hernández-López, E. Bospuez-Molina
B. Mirza, J. Mol. Struct., 2017, 1149, 720–726. and C. L. Wilson, Crop Protect., 2003, 22, 1087–1092.
37 S. Shujah, Zia-ur-Rehman, N. Muhammad, A. Shah, S. Ali, 62 Z. Jia, D. Shen and W. Xu, Carbohydr. Res., 2001, 333, 1–6.
N. Khalid and A. Meetsma, J. Organomet. Chem., 2013, 63 C. J. Gu, W. H. Wu, F. C. Wang and M. F. Zhu, Macromol.
741–742, 59–66. Symp., 2007, 254, 160–166.
38 M. Shabbir, Z. Akhter, I. Ahmad, S. Ahmed, H. Ismail, 64 M. Shabbir, Z. Akhter, I. Ahmad, S. Ahmed, M. Bolte,
B. Mirza, V. McKee and M. Bolte, J. Mol. Struct., 2016, H. Ismail and B. Mirza, Inorg. Chim. Acta, 2017, 463, 102–
1116, 84–92. 111.
39 D. Bandyopadhyay, M. Layek, M. Fleck, R. Saha and 65 M. Zaheer, A. Shah, Z. Akhter, R. Qureshi, R. Mirza,
C. Rizzoli, Inorg. Chim. Acta, 2017, 461, 174–182. M. Tauseef and M. Bolte, Appl. Organomet. Chem., 2011,
40 A. Prakash, B. K. Singh, N. Bhojak and D. Adhikari, 25, 61–69.
Spectrochim. Acta, Part A, 2010, 76, 356–362. 66 R. Xu, B. Aotegen and Z. ZhongInt, Int. J. Biol. Macromol.,
41 M. L. Low, L. Maigre, M. I. M. Tahir, E. R. T. Tiekink, 2017, 105, 1563–1571.
P. Dorlet, R. Guillot, T. B. Ravoof, R. Rosli, J. M. Pages, 67 H. E. Salama, G. R. Saad and M. W. Sabaa, Int. J. Biol.
C. Policar, N. Delsuc and K. A. Crouse, Eur. J. Med. Chem., Macromol., 2015, 79, 996–1003.
2016, 120, 1–12. 68 M. W. Sabaa, A. M. Elzanaty, O. F. Abdel-Gawad and
42 B. S. Creaven, E. Czegledi, M. Devereux, E. A. Enyedy, E. G. Arafa, Int. J. Biol. Macromol., 2018, 109, 1280–1291.
A. F.-A. Kia, D. Karcz, A. Kellett, S. McClean, N. V. Nagy, 69 R. F. M. Elshaarawy, A. A. Refaee and E. A. El-Sawi,
A. Noble, A. Rockenbauer, T. S. O-Planka and M. Walsh, Carbohydr. Polym., 2016, 146, 376–387.
Dalton Trans., 2010, 39, 10854–10865. 70 N. Mala and K. Pramendra, Dalton Trans., 2011, 40, 7077.
43 M. Nath and P. K. Saini, Dalton Trans., 2011, 40, 7077. 71 K. Xhanari and M. Finšgar, RSC Adv., 2016, 6, 62833–62857.
44 M. Mesbah, T. Douadi, F. Sahli, S. Issaadi, S. Boukazoula 72 J. O. Bockris and D. A. J. Swinkels, J. Electrochem. Soc., 1964,
and S. Chafaa, J. Mol. Struct., 2018, 1151, 41–48. 8, 736–743.
45 B. Iikhar, K. Javed, M. S. U. Khan, Z. Akhter, B. Mirza and 73 X. Li, S. Deng, H. Fu and T. Li, Electrochim. Acta, 2009, 54,
V. Mckee, J. Mol. Struct., 2018, 1155, 337–348. 4089–4098.
46 K. S. Kumar, S. Ganguly, R. Veerasamy and E. De Clercq, 74 M. P. Desimonea, G. Grundmeierb, G. Gordilloc and
Eur. J. Med. Chem., 2010, 45, 5474–5479. S. Simison, Electrochim. Acta, 2011, 56, 2990–2998.
47 O. Güng and P. Gürkan, J. Mol. Struct., 2014, 1074, 62–70. 75 K. Xhanari and M. Finsgar, RSC Adv., 2016, 67, 62833–
48 R. F. M. Elshaarawy, T. B. Mostafa, A. A. Refaee and E. A. El- 62857.
Sawi, RSC Adv., 2015, 5, 68260–68269. 76 W. A. Zoubi, J. Coord. Chem., 2013, 66, 2264–2289.
49 A. A. Shanty, J. E. Philip, E. J. Sneha, M. R. P. Kurup, 77 A. S. Yaro, A. A. Khadom and R. K. Wael, Alexandria Eng. J.,
S. Balachandran and P. V. Mohanan, Bioorg. Chem., 2017, 2013, 52(1), 129–135.
70, 67–73. 78 U. R. Evans, The Corrosion and Oxidation of Metals, Hodder
50 K. V. Shuvaev, L. N. Dawe and L. K. Thompson, Eur. J. Inorg. Arnold, 1976.
Chem., 2010, 29, 4583–4586. 79 P. Singh and M. A. Quraishi, Measuremen, 2016, 86, 114–
51 K. H. M. E. Tehrani, M. Hashemi, M. Hassan, F. Kobarfard 124.
and S. Mohebbi, Chin. Chem. Lett., 2016, 27, 221–225. 80 A. Yurt, B. Duran and H. Dal, Arabian J. Chem., 2014, 7, 732–
52 K. M. Khan, M. Khan, M. Ali, M. Taha, S. Rasheed, 740.
S. Perveen and M. I. Choudhary, Bioorg. Med. Chem., 2009, 81 T. K. Chaitra, K. N. S. Mohana and H. C. Tandon, J. Mol.
17, 7795–7801. Liq., 2015, 211, 1026–1038.

This journal is © The Royal Society of Chemistry 2018 RSC Adv., 2018, 8, 23294–23318 | 23317
 View Article Online

RSC Advances Review

82 P. M. Dasami, K. Parameswari and S. Chitra, Measuremen, 101 D. K. Singh, E. E. Ebenso, M. K. Singh, D. Behera,
2015, 69, 195–201. G. Udayabhanu and R. P. John, J. Mol. Liq., 2018, 250,
83 A. Yurt, A. Balaban, S. Ustün Kandemir, G. Bereket and 88–99.
B. Erk, Mater. Chem. Phys., 2004, 85, 420–426. 102 H. M. A. El-Lateef, A. M. Abu-Dief, L. H. Abdel-Rahman,
84 M. Behpour, S. M. Ghoreishi, N. Soltani and M. Salavati- E. C. Sañudo and N. Aliaga-Alcalde, J. Electroanal. Chem.,
Niasari, Corros. Sci., 2009, 51, 1073–1082. 2015, 743, 120–133.
85 I. Ahamad, R. Prasad and M. A. Quraishi, Corros. Sci., 2010, 103 S. Omanovic and M. Metikos-Hukovic, Solid State Ionics,
52, 933–942. 1995, 78, 6.
86 O. Olivares, N. V. Likhanova, B. Gomez, J. Navarrete, 104 M. Behpour, S. M. Ghoreishi, M. Salavati-Niasari and
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

M. E. Llanos-Serrano, E. Arce and J. M. Hallen, Appl. Surf. B. Ebrahimi, Mater. Chem. Phys., 2008, 107, 153–157.
Sci., 2006, 252, 2894. 105 A. A. Farag and M. A. Hegazy, Corros. Sci., 2013, 74, 168–
Open Access Article. Published on 27 June 2018. Downloaded on 6/4/2021 [Link] PM.

87 M. Prajila and A. Joseph, J. Mol. Liq., 2017, 41, 1–8. 177.

88 H. M. A. El-Lateef, A. M. Abu-Dief and M. A. A. Mohamed, 106 E. E. Oguzie, Y. Li and F. H. Wang, Corros. Sci., 2007, 310,
J. Mol. Struct., 2017, 1130, 22–542. 90–98.
89 N. K. Gupta, C. Verma, M. A. Quraishi and A. K. Mukherjee, 107 M. Heydari and M. Javidi, Corros. Sci., 2012, 61, 148–155.
J. Mol. Liq., 2016, 215, 47–57. 108 N. Soltani, M. Behpour, S. M. Ghoreishi and H. Naeimi,
90 S. Vikneshvarn and S. Velmathi, Surf. Interfaces, 2017, 6, Corros. Sci., 2010, 52, 1351–1361.
134–142. 109 K. Benbouguerra, S. Chafaa, N. Chafai, M. Mehri,
91 S. R. Gupta, P. Mourya, M. M. Singh and V. P. Singh, O. Moumeni and A. Hellal, J. Mol. Struct., 2018, 1157,
J. Organomet. Chem., 2014, 767, 136–143. 165–176.
92 E. E. Elemike, H. U. Nwankwo, D. C. Onwudiwe and 110 S. Safak, B. Duran, A. Yurt and G. Türkoğlu, Corros. Sci.,
E. C. Hosten, J. Mol. Struct., 2017, 1147, 252–265. 2012, 54, 251–259.
93 E. E. Elemike, H. U. Nwankwo and D. C. Onwudiwe, J. Mol. 111 A. Aytaç, Ü. Özmen and M. Kabasakaloğlu, Mater. Chem.
Struct., 2018, 1155, 123–132. Phys., 2005, 89, 176–181.
94 M. Behpour, Corros. Sci., 2008, 50, 2172–2181. 112 A. Yurt, S. Ulutas and H. Dal, Appl. Surf. Sci., 2006, 253, 919–
95 E. E. Elemike, H. U. Nwankwo, D. C. Onwudiwe and 925.
E. C. Hosten, J. Mol. Struct., 2017, 1147, 252–265. 113 G. Khan, S. N. Kazi, W. J. Basirun, G. M. Khan and
96 K. F. Khaled, Electrochim. Acta, 2010, 55, 6523–6532. P. Ahmed, Aust. J. Basic Appl. Sci., 2015, 9, 131–138.
97 S. Mo, L. J. Li, H. Q. Luo and N. B. Li, J. Mol. Liq., 2017, 242, 114 H. Ashassi-Sorkhabi, B. Shabani, B. Aligholipour and
822–830. D. Seifzadeh, Appl. Surf. Sci., 2006, 252, 4039–4047.
98 I. Danaee, O. Ghasemi, G. R. Rashed, M. Rashvand Avei and 115 W. A. Zoubi and Y. G. Ko, ACS Sustain. Chem. Eng., 2018, 6,
M. H. Maddahy, J. Mol. Struct., 2013, 1035, 247–259. 3546–3555.
99 U. J. Naik, P. C. Jha, M. Y. Lone, R. R. Shah and N. K. Shah, 116 W. A. Zoubi, J. H. Min and Y. G. Ko, Sci. Rep., 2017, 7, 7063–
J. Mol. Struct., 2016, 1125, 63–72. 7077.
100 M. A. Hegazy, A. M. Hasan, M. M. Emara, M. F. Bakr and
A. H. Youssef, Corros. Sci., 2012, 65, 67–76.

23318 | RSC Adv., 2018, 8, 23294–23318 This journal is © The Royal Society of Chemistry 2018