chemistry of schiff bases - shodhgangashodhganga.inflibnet.ac.in/bitstream/10603/33335/14/7 chapter-...
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CHEMISTRY OF SCHIFF BASES:
The consideration products of carbonyl compounds and primary amines are often
named as Schiff bases. They are also known as azomethines or anils or imines.
Schiff bases can be prepared by (i) The reaction of carbonyl groups with amino
groups are related reaction, (ii) nitroso-methylene condensation, (iii) formation of oximes via
c-nitro sations, (iv) diazonium salt-methylene condensations, (v) additions to carbon-carbon
double or triple bonds, (vi) formation of >C=N bands through ylids, (vii) tautomerization of
amides and thioamides are related reactions, (viii) addition reactions to nitriles, isonitriles,
nitrile oxides and related compounds, (ix) oxidation and elimination from nitrogen
compounds, (x) reduction of nitro compounds, (xi) formation of azomethine by
rearrangements and photochemical reactions and (xii) electrochemical synthesis at lead
electrode.
The condensation of primary amines with carbonyl compounds was first reported by
Schiff [1]. The reaction was reviewed [8, 286]. The experimental conditions depend on the
nature of the amine and the carbonyl compounds which determine the position of the
equilibrium.
The reaction was reviewed [4, 55]. The experimental conditions depend on the nature
of the amine and the carbonyl compounds which determine the position of the equilibrium.
RR’CO+R”NH2 RR” C=NR”+H2O
Usually, it is advisable to remove the water as it is formed by distillation or by using
an azetrope forming solvent [10, 18, 211]. This is necessary with diaryl or aryl alkyl ketones,
but aldehydes and dialkyl ketones can usually be condensed with amines without removing
the water. Aromatic aldehydes react smoothly under mild conditions and at relatively low
temperatures in a suitable solvent or without it. In condensations of aromatic amines with
aromatic aldehydes, electron attracting substituents in the para position of the amine decrease
the rate of the reaction, while increasing it when on the aldehyde [50]. In both cases a linear
sigma-rho relationship was observed. With ketones, especially with aromatic ones, higher
temperatures, longer reaction times and a catalyst are usually required in addition to the
removal of water it is formed.
The reaction is acid catalysed. However, only aldehydes and ketones which do not
aldolize easily in acidic media can be condensed with amines in the presence of strong acid
catalyst, eg., concentrated protic acid [39], BF3 – ETHERATE [49, 219], Zncl2 [2, 18, 20, 39,
55] or POCl3 [51]. For methyl ketones, only weak acids should be used, while for methylene
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ketones, which are less sensitive to acid catalyzed aldolizations, stronger acids may be used
as catalysts [4]. Ultraviolet irradiation is reported [20] to promote the formation of
azomethines from aldehydes. This is explained [57] as a light promoted auto oxidation of part
of the aldehyde to the corresponding acid, which in turn acts as catalyst. Schiff bases have
also been prepared using piperidine [215], dimethylacetamide and 5% lithium chloride [265]
and platinum group elements [335] as catalysts. Aromatic aldehydes and aliphatic or aromatic
ketones give with the amines quite stable azomethines. Primay apliphatic aldehydes can give
azomethines with various amines if the reaction is carried out at 00C, and the product’ is
distilled from KOH [11, 17]. The effect of solvent in the preparation of Schiff bases was also
studied as a function of the Reichardt ETN and modified Kamlet-Taft BKT parameters by
Nagy et al [313].
The intra nuclear distance quoted for the >C=N-double bond is 1.29A0 for the non-
conjugated group and 1.35 or 1.36 A0 for azo-aromatic compounds [37]. Symth [3.25]
estimated the dipole moment of >C=N-to be 0.9 D.Cottrell [40] calculated the bond energy
for C=N-bond from the original data of Coates and Sutton [12] and found to be
147.0K.cal/mole. Palmer’s book [42] gave some detailed examples of the calculation of bond
energies from thermochemical data and found to be 142.0K.cal/mole
The IR data found in the literature revealed that the acyclic >C=N- bond most
commonly encountered in Schiff’s bases (azomethines) absorb in the 1690-1640 cm-1 region.
In most cases it is a strong and fairly sharp band located at somewhat lower frequencies than
the bands of carbonyl groups and close to >C=C, stretching frequencies. In the absence of
strain, steric hindrance or other complicated factors and in dilute solutions, prepared from
neutral solvent, the stretching frequency of >C=N-is found to be 1670 cm-1 the corresponding
force constant, 10.6 dynes cm-1 is in the harmonic oscillator approximation. If there are one or
more groups conjugated with the >C=N- group the frequency is usually lowered. Generally
speaking there is very little difference between infrared and Raman frequencies and between
the spectra of pure liquids and solids and their solutions in CCl4 or other not very associative
solvents. In general >C=N-vibrations exhibit a lesser degree of localization than >C=O
vibrations.
Little is known about the electronic spectrum of the C=N group itself in a purely
aliphatic environment.Platt [31]and Sidman [38] estimated that -n transition lies at 2100 A0
if the >C=N-group carries only aliphatic substances, at 2500 A0 if conjugated with vinyl
group and at 2900 A0 on a benzene ring. Much more is known about the spectra of
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compounds in which the >C=N-group is substituted by aromatic rings. Charette, Faltlhanal
and Teyssie [55] studied the ultraviolet spectra of a series of N-salicylidene alkyl amines and
their aryl-substituted derivatives in different solvents. Spectacular changes occur when the
inert solvents are replaced by hydrogen bonding solvents. Gawinecki, Ryazard et al prepared
some Schiff Bases derived from aryl groups and carried out the UV studies [189]. Kinetics
and mechanism of hydrolysis of Schiff bases were studies by Pishchugin et al [261, 262].
Hydrolysis of various oxazolidines and N-acylated oxazolidines was carried out to explosure
that suitability as potential prodrugs [285]. Mohammed et al. reported the kinetics of
hyrolysis of Schiff bases and indicated that the rate-determining step is changed from –OH
attack on the free Schiff base in alkaline media to attack by water on the protonated Schiff
base in neutral and weakly acidic media. The results of study of solvent effect on base
hydrolysis rates suggest that specific solute-solvent interactions, viz., dispersion forces and
intermolecular hydrogen bonding play important roles [287]. Pramila and coworkers
examined the rates of hydrolysis of Schiff bases at pH 4-13 in a 10% dioxime water system
and in various non-ionic surfactant systems [433]. Angles et al studied the hydrolysis of
Schiff bases in aqueous and non-aqueous media [440].
Determination proton-ligand stability and stability of Schiff bases were reported in the
literature [62, 72,122,123,130,154,317,358]. Salman et al [441] studied some new o-hydroxy
Schiff bases in four solvents using UV spectra and reported that the appearance and intensity
of band at >400 nm which belongs to the keto form of the Schiff base depends on the
electronic and not the steric effect of the substituent. Potentiometric investigation of effects of
several electron donating and withdrawing substitutents on the basicity of azomethine group
of salicyalidene aniline in nitrobenzene was carried out by Gunduz et al [336]. Potentiometric
study of some Schiff base ligands was reported in the literature [337] Madhav et al [419]
studied some Schiff bases using HMDE, square wave and cyclic Volta metric techniques and
explained the results in terms of electron withdrawing and releasing effects of the substituted
groups. Effects of supporting electrolytes, solvents and acid concentration on salicyladehyde
tris Schiff base have been studied polagraphically by Sreenivasulu et al [420].
By virtue of the presence of lone-pair of electron on the nitrogen atom and of the
general electron donating tendency of the double bond, compounds containing the
azomethine group should possess basic properties. The most characteristic aspect of the
compounds containing the >C=N-group which show basic properties lies in the formation of
complexes with metals. These complexes provide some very characteristic series of
coordination compound. The basic strength of the >C=N-group is inadequate by itself to
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permit the formation of stable complexes by simple coordination of the lone pair of electrons
to a metal ion. Therefore, in order that stable compounds to be formed it is necessary that
there should also be present in the molecule a functional group with a replaceable hydrogen
atom, preferably a hydroxyl group near enough to the >C=N- group to permit the formation
of a five or six membered ring by chelation to the metal atom.
Physico-chemical studies of Metal-Schiff base complexes:
A perusual of literature revealed that Schiff bases behave as monodentate, bidentate
and polydentate ligands towards many metal ions in the formation of complexes. Metal
chelates of azomethines mostly with transitional metals, lanthanides and rare earths have
been prepared and characterized using elemental analysis, conductometry, magnetic
susceptibility, thermal (TG, DTA, DSC), X-ray diffraction, X-ray fluorescence, infrared,
ultraviolet visible, mass, nuclear magnetic resonance, electron spin resonance and proton
resonancespectra [61, 67, 70, 80, 82, 93, 97, 100, 103, 110, 121, 125, 132, 136, 139, 140,
146, 152, 156, 162, 163, 169-172, 174-185, 197, -212, 215-234, 236-239, 241-248, 252-254,
256-260, 298-301, 319, 363, 479].
The characterization of metal Schiff base complexes synthesized electro-chemically
has also been reported [293, 318, 401, 422, 434, 436]. Formation of polynuclear and mixed-
ligand copper (II) complexes with Schiff base have been envisaged in the literature
[303, 475].
Studies of metal-azomethine complexes in solution have been carried out by several
authors. Metal –to-ligand ratio and stability constants for the complexes were computed using
pH metric and potentiometric [62, 72-74, 88, 96, 122-125, 129, 133, 148, 155, 157, 168, 196,
235, 316, 336, 352, 383, 397-399, spectrophotometric [60, 75, 104, 150, 196, 260, 262, 317]
and conducto metric [408] techniques.
Solvent extraction, thin layer chromatography and spectro electrochemical studies
were carried out to study Cu (II), Zr(IV), U(VI), Co(II) and Th (IV) Schiff base complexes
[64, 126, 195, 233]. Schiff bases were also used in the fluoremetric determination of
beryllium [228] and aluminium [281]. Aoki et al studied the effect of metal-to-liand ratio on
fluorescence properties of Zn (II) and Be(II) Schiff base Complexes[314]. The same authors
have also determined ethylenediamine fluoremetrically by forming a fluorescent Be(II) Schiff
base complex [396].
Polarographic technique has also been employed by various authors in the study of
metal-azomethine complexes to determine coordination number, stability constants, kinetic
parameters and stereochemical behavior in solution for reversible and irreversible systems
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[9, 64, 87, 127, 130, 131, 134, 135, 137, 143, b147, 149, 158, 159, 186, 190, 193, 222, 249,
250, 287, 291, 307, 350, 407, 412, 442].
Applications of Schiff bases and their metal complexes:
The >C=N-group is present in may organic molecules of fundamental importance.
They have got extensive application in biological and industrial fields. Schiff bases with
potential pharmaceutical use were synthesized [26,29,46]. Anticataract pharmaceutical Schiff
bases have been reported by Elsmer et al [292]. Azomethines prepared by Nakahara and his
coworkers were used as catalysts providing dental composites with excellent hardens,
adhesion, on dentin and enamel, and discolouration resistance [306]. Thirty seven
pharmaceutical anils were reported in the literature possessing anti inflammatory, antipyretic
and analgesic properties [84]. Neomycin derivatives were recovered by converting them to
Schiff bases with aromatic aldehydes at PH<7.0. These Schiff bases themselves are useful in
human and verterinary medicine [46]. A potentcy of 725 streptomycin units/mg was reported
for a number of Schiff bases prepared from salt of streptomycin [47]. Compounds of pencillin
with Schiff bases of amphetamine were reported [23]. Therapeutically effective Schiff bases
exhibiting cardio tonic and diuretic actions have also been prepared [8, 36, 114]. Schiff bases
having anti inflammatory property have been synthesized [41, 220, 227]. Sivam et al
prepared some Schiff bases useful as raw materials for drugs, agrochemicals and electron
devices by reduction of them with molecular hydrogen in presence of palladium containing
catalyst and tertiary amines.
Tuberculostatically active Schiff bases were condensed from aldehydes and amines
with activity at 10-6, 10-7 concentration [19, 35, 98]. Shah et al reported potential
tuberculostatic azomethines which inhibited growth of mycobacterium tuberculosis in vitro
[283].
Antiviral active anils were prepared in presence of zinc and acetic acid by Auelbekov
et al [229]. Iridium (III) Schiff base complexes also behaved as antivirucides [312].
Substituted salicyladehyde Schiff bases of 1-amino-3hydroxy guamidine tosylate acted as
antiviral against cornovirus.
Fifty seven Schiff bases used as anticancer agents were reported by Chaudari and his
coworkers [105]. Anticancer activity of Schiff bases was also cited in the literature [161].
Schiff bases of uracil-6-carboxaldehyde were synthesized and evaluated as potential
antitumour agents by Kim et al [445]. Metal-Schiff base complexes studied by Zishen et al
also exhibited anticancer activity against Ehrlich ascites carcinoma, with the Cu(II)complexes
having the highest activity [358]. Pronounced anticarcinogenic reactivity of copper-di-Schiff
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bases has been studied [389]. Antineoplastic properties of different Schiff bases have been
examined both in vitro and in vivo and reported as useful future anticancer agents [391].
Copper complexes of di-Schiff bases were used as neoplasm inhibitors and antirheumatics
[361, 392]. Schiff bases derived from salicylaldehyde and 2-substituted aniline and their
metal chelates with Cu(II), Ni(II) and Co(II) ions were screened for antiulcer activity. The
copper complexes showed an increased activity [309].
Insecticidal compositions containing Schiff base as an active ingredient was reported
[5]. The anils alone did not exhibit grater insecticidal action prepared by West [6] but exerted
enhanced effect on non-aqueous solutions containing pyrethrum or rotenone. Thirteen
azomethines tested against several pathogenic fungi were reported [22]. Schiff bases
possessing pesticidal and fungicidal activity were reported by Gradon and coworkers [160].
Quantitative estimation of azomethine containing insecticides and fungicides was carried out
polarographically [142]. Synthesis of some more Schiff bases of fungicidal activity were also
reported [49, 144, 175, 187, 275-277, 298, 322, 347, 348, 359, 362]. Siddique et al. [329]
evaluated the toxicities of Schiff bases and their complexes against insects and also reported
the greater efficacy for the complexes than the Schiff bases.
Complexes with bidentate Schiff bases were reported to possess biocidal activity
against bacteria and fungi [194, 577]. Singh and his coworkers synthesized some boran
complexes with Schiff bases and found to possess antifungal and antibacterial activity [352].
Schiff bases derived from methylcyclo propyl ketones on addition with dialkyl phosphates
showed aphicidal activity [380]. Twenty six thiazole Schiff bases and derivatives prepared by
Mehapatra showed antifungal activity curvularia species [214] “Schiff base complex of
copper possessing considerable high fungi toxicity was reported by Satpahty et al “[465]. The
antifungal property of some nickel-Schiff base complexes was studied. The complexes were
more active than the free ligands against all the fungi tested [290]. Fifteen transition metal
complexes with three Schiff bases have been screened against some fungal pathogens.
Among these, Cu(II) and Co(II) complexes with one of the three Schiff bases, namely benzyl-
touldine ligand showed high fungi toxic results [360]. Schiff bases derived from 5-nitro and
5-chloro salicylaldehyde and their complexes with Mn(II), Fe(III), Ni(II) and Cu(II) have
been studied for fungicidal activity using the growth method [321., 346]. A serried of sixteen
methylated polyfluoro aromatic Schiff bases and their salts were tested as acaricides,
fungicidies and insecticides. Fluorination on the aldehyde part of the molecule enhanced the
insecto acaricidal activity over that caused by fluorination on amine part [375]. Schiff base
obtained from Tries and glyoxal was studied for its pesticidal activity by Nicolae et al [188].
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Pesticidal active phosphonium salts of C-phosphorous (III) substituted azomethines were
synthesized [441].
Bactericidal and chemotherapeutical active Schiff bases were prepared from
sulfaphyridine [8,114]. Schiff bases with antibacterial activity derived from different
aldehydes and amines were cited in the literature [13,14, 83-85]. Of the seventy-three
azomethines prepared by Tottistrov et al, only salicylaldehyde component possessed Schiff
bases were found to contain antimicro biological activity [65]. Schiff bases having
antibacterial activity were prepared and reported by various workers [28, 239, 294, 297, 315,
49, 354,355,384,388,394,410,421,424,430].
Amino acid Schiff base complexes of dimethyl dichlorosilane were prepared and
studied their antibacterial activity. The data showed that the silane complexes were better
inhibitors than the corresponding free ligands [213]. Antibacterial activity of Schiff bases and
their metal complexes, varied from inacntive to highly active, was discussed with regards to
ligands and metal content [263]. Antimicrobial activity of coordination compounds of some
3d elements with Schiff bases was tested against strains of staphylococcus, proteus,
salmonella, shigella and vaccine strains of a Bacillus authraris [356]. Schiff base complexes
of uranium and ziroconium were examined for antibacterial activity in vitro [296].The
antimicrobial activity four bacteria strains were studied using diffusion test procedure [295].
Mester et al. prepared ten Schiff bases possessing trypnosomical activity [307].
Schiff bases possessing herbicidal activity were prepared by Sinha et al [320].
Azomethines were also used as starting material and intermediates in the preparation of
herbicides [270, 27]. It is found that Schiff bases have been employed as growth regulators
[106]. D’Amico prepared six Schiff bases and found to be useful as plant growth regulators.
Schiff base of aminohydroxy tetrahydronaphalene was found to possess growth regulating
activity [31].Growth regulating activity of Schiff bases on cucumbers and tomatos [273] have
been studied. Some azomethine compounds used as growth stimulants were also reported
[230].
Salicyladehyde - tryptohan complex of copper (II) has been used as a tool for
immobilization of protein [339, 340]. Syntheses of new cataionic Schiff base complex of
copper (I) and their selective binding with DNA was reported by Janak et al [481]. Radio
labeled Schiff bases were used brain studies and their lipophilicity and protein binding
capacity have been demonstrated [226]. The role of cell-surface Schiff base forming ligands
in the inductive interaction between Class II*antigen Presenting cells (APC) and murine T
cells was investigated [382]. A review with 47 references was presented on bioinorganic
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chemistry of metal-Schiff base chelates as vitamin B6 analogs [92].Azomethines with
anticoagulant properties were reported in the literature [316, 385-387, 415].
Mixtures of linear poly Schiff bases of low molecular weight were synthesized from
aliphatic diamines and terephthaldehyde [30]. Soluble and insoluble polymeric Schiff bases
were synthesized and their Co(II), Cu(II) and Ni(II) complexes were characterized [173].
Diamagnetic polymeric Schiff base complex of Zn and Uo2+ Complexes were prepared by
Mishra and his coworkers [475]. Cross linked polymers from Schiff bases have been derived
and reported by Barbara andhis coworkers [278]. Al-Dujali et al synthesized liquid crystalline
poly Schiff base polymers [430, 404]. Polymers of azomethine group containing methyl
acrylate esters were prepared by Ohashi et al [438, 439] and used for second harmonic
generation devices in opto-electronics.
Mixtures of azomethines and diazomethane pigments were used for PVC, printing
inks and coasting with good migration resistance [99,138]. Azomethines and their metal
complexes with Cu(II), Ni(II), Zn(II) and Co(II) reported by Hunger were used as pigments
[145]. The Schiff base derived from salicylaldehyde and diaminomaleonitrile and its metal
complexes were used as pigments [138, 279]. Some azomethine transitional metal chelates
useful as pigments for plastics were also cited in the literature [84]. Theodar [108]
synthesized fast greenish yellow to bluish red diazomethane pigments. Azomethine-metal
complexed pigments from bibenzyl series have been prepared [405].
Paints containing drying oils with conjugated double bonds and Schiff bases were
reported [34]. Property to Schiff bases increasing the drying rate of paints was cited in the
literature [33]. Schiff base compounds useful for electrophoretic coating [309] and corrosion
inhibitors [324, 447] were also reported.
Polyazomethine dyes were synthesized by Streel and Reindl [44]. Azomethines were
used for dyeing and printing of fibrous material from polymers or copolymers of acrylonitrile
or dicyanethylene [28]. Schiff base metal complexes containing azo groups have been
prepared and used as dyes for cotton, polyster, wool and leather [222, 224]. Chromium Schiff
base complexes have been used as fast brown dye for wooll and leather [223]. Metal chelates
of Group IV elements with Schiff base ligands have been synthesized and reported as
colouring material for resins [305]. Complexes of O-phenylenediamine bis {salicylaldimine
with Fe(III), Ni(II), Cu(II) useful as intermediates for drugs, agro chemicals, porphyrins and
dyes [375, 413]. Bis (hydroxyl benzylidene amino) benzene sulfonamide derivatives of metal
complexes were used for mass dyeing of polyester fibres [225]. Schiff bases were also used
to promote the light-fastness of syntheitic threads, fibres and foils [41]. Complexes of
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azomethines useful for improving the light fastness of dyed leathers were synthesized [264].
Schiff bases as luminescent dyes for solar collectors were also reported [402]. Copper
complexes of Schiff bases derived from Phenolic aldehydes with aliphatic diamines were
used as good light stabilizers for dyed and undyed polyamide Fibres [373]. In photography,
a yellow Schiff base was used inirreversibly dischargeable photographic filter and
antihelation layers as filtering agents [24]. Anils formed yellow styryl dyes particularly useful
for colour correction masks for the cyan layer of colour film [27]. Photographic developers
incorporating azomethine group were also described [15]. Certain Schiff baes of dialdehyde
and diamino compound, when mixed with gelatin were used as colour filter in making colour
films [16]. Schiff bases prepared by Mariko and Sadao showed goodmiscibility in various
resins, have good solubility and were used in the charge transferring layer of
electrophotographic photoreceptors [267]. Substituted azomethines were also employed in the
coating of electrophotographic paper [45]. Some caionic technetium complexes o f Schiff
base ligands were studied as myocardial imaging agents [269].
Schiff base compounds useful as aroma and taste enhancers in perfurmes, cosmetics,
food stuff, chewing gums and beverages were prepared [328, 344,345]. Schiff bases derived
from amines and organoleptically acceptable aldehydes were employed as deodorants for
removing aldehyde associate off flavor in fats, oils [374] and odourous air from refrigerators
or raw garbage [342, 415].
Aromatic polyazomethines were used in the manufacture of filaments [265].
Dicarboxylic acid azomethines were reported and used in the preparation of high glass
temperature materials from apoxy resins [272]. Heat and fire resistant polyazomethines have
also have also been prepared [326, 343, 372, 416]. Rajan carried out studies on the
application of Schiff bases for high temperature lubrication [409]. Heat resistant
polyazomethines with good electrical properties and useful for manufacturing printed circuit
boards were prepared by Kihara et al [414]. The polymeric Schiff bases synthesized were
found to posse’s semiconducting properties [76]. A review with seven references on organic
semiconductors prepared from polymeric Schiff bases was discuassed [218]. Yasuo et al
prepared six thermostable and semiconducting polyazomethines by poly condensation of
diamines with dialdehydes [379]. Nishikawa et al prepared Schiff base type epoxy
compounds with excellent heat resistance, mechanical strength and optical characteristics and
were used for laminates, coating and semi conduction sealants [377, 378,443]. Schiff bases
were also used in the preparation of automobile antiglare mirros [266]. Anils derived from
heterocyclic carbonyl compounds with 2,6-diethylamine were used as rubber antioxidants
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[219]. Modified rubber compositions with improved green strength and cured properties and
useful for tires, were manufactured by treating unsaturated rubbers with Schiff bases in the
presence of a Friedel-Crafts catalyst and then adding carbon black [325].
Schiff bases was used as catalysts in accelerating the formation of the factice [21, 86,
109]. Organic compound containing an azomethine group was used as a catalyst for the
polymerization of H2CO in an inert medium [48]. The catalytic and oxidative activities of
azomethines and their corresponding copper, nickel chelates were discussed by Aptekar et al
[71]. Rhodium- salicylidene complexes and nickel-azomethine complexes used as catalysts
for isomerization and dimerization of -olefins respectively were reported [86, 109]. The
liquid phase oxidation of 2,3,6-trimethyphenol to 2,3,6-trimethyal-pquinone with molecular
oxygen catalyzed by metal- Schiff base complexes were performed in various solvents by
Mizukami et al [318]. Titanium (IV)-Schiff base complexes were employed as catalysts in the
oxidation of thianisole [282]. Optically active quadridentate Schiffbases and their titanium
(IV) complexes were prepared by Caoriet al and employed as catalyst in the asymmetric
oxidation of methyl phenyl sulphide with organic hydroperoxides [425]. Ring opening
reactions of epoxides with trimethylsilyl cyanide catalyzed by titanium alkoxide - Schiff base
complexes were studied by hayashi et al [446]. Catalytic dehydrogenation of hydrozones to
diazo compounds was carried out with cobalt Schiff base complex-oxygen system [280].
Catalytic efficiency of Cobalt (II) complexes of tetra and unique denate Schiff base ligands
had been tested towards the oxidation of 2,6-di-tert-butyl phenol by molecular oxygen
[320, 341]. In the oxidation of 3,5-di-tert-butyl catechol to 3,5-di-tert-butyl cquinone,
complexes of UO2(II), Cu(II) and Ni(II) with complexes which are less active than their
Cu(II) analogs and used as catalysts in the oxidation of 3,5-di-tert-butyl catechol by oxygen
[423]. The mechanism of oxygen binding by cobalt (II) complexes with bidentate Schiff
bases was considered by Vogt et al. [217]. Pallidum complexes of Schiff bases derived from
heterocyclic aldehydes were used as catalysts for the hydrogenation and isomerization of allul
benzene in methanol in presence of NaBH4 [304]. Stable peroxo Schiff base complexes of
thorium [364] and Zirconium [365] were tested for their catalytic activity. Bis (salicylidene)-
1,2-diaminocyclohexane-Mn(III) complex was synthesized and its catalytic property was
studied [371]. Cobalt-Schiff base complexes were used as metal complex carriers of oxygen
[217, 368]. Du, Wen et al carried out the catalytic oxidiation of phenols by cobalt-Schiff base
complexes [370]. Epoxidation of olefins catalysed by mono-and bi-nuclear Schiff base
complexes was reported and the catalytic activity was correlated with the structure of the
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ligand, the redox potential of the metal ion and the binuclear character of the complex
[367, 369, 400]. Reductive carbonylation of nitrobenzene to phenyl urethane catalyzed by
ruthenium (III) Schiff base complex was reported by Khan et al [366]. Schiff base complex of
ruthenium (III), useful as catalytic organic oxidant was prepared [437]. Epoxidation of
alkenes with iodosylbenzene using mono-and binuclear ruthenium (III) Schiff base complex
catalysts is studied by Upadhyay et al [444].
In addition to the above mentioned applications, Schiff bases have been employed in
preparative uses, (e.g.heterocyclic compounds) [381] for the identification, detection and
determination of aldehydes or ketones, for the purification of carbonyl or amino compounds
(amino acids in protein hydrolysats) [7], or for the protection of these groups during complex
of sensitive reactions (e.g.amino acids during peptide synthesis) [53]. Primary amines were
determined by Fluorescent high performance liquid chromatography and chemiluminescene
flow injection methods after converting them s Schiff bases [406, 431,432]. The condensed
project of salicylaldehyde with o-amino phenol was used as a gravimetric reagent for copper
(II) [107]. Metallic impurities, such as copper from petroleum products were removed using
Schiffbases [32]. In bioprosthetic tissue, residual aldehyde levels, which when high may
cause implantation problems such as inflammation and other adverse reactions, were reduced
in the form of Schiff base by contacting the tissue with a rinsing solution containing a
primary amine [323].
Iron is the fourth most abundant element in the earth´s crust occurring in nearly all
types of rock and soil minerals as both Fe Iron is the fourth most abundant element in the
earth´s crust occurring in nearly all types of rock and soil minerals as Fe 2+ both Fe3+ Iron
plays a central role in the biosphere, serving as the active center of proteins responsible for O
and electron transfer and of metalloenzymes such as oxidases, reductases and dehydrases
[476].
In recent years several studies have linked the concentrations of specific transition
metal ions to various diseases. Low serum copper level is used as a marker for wilson´s
disease. Serum copper levels are elevated in a large number of chronic and acute illnesses
such as Hodgkin´s disease, leukemia, and many other malignancies [439]. Zinc is an
important nutritive factor as well as a cofactor for many metalloenzymes. Zinc is necessary
for the growth and division of cells, especially during the stages of life when growth rates are
high. Zinc deficiency is associated with syndromes that cause short stature and dwarfism
[113]. Also, iron and cobalt are all trace essential elements for human bodies. These essential
elements can induce some diseases while it is harmful and deleterious for overtaken [506].
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A new modeling study of the role of transition metal ions on cloud chemistry has been
performed. Developments of the model of multiphase cloud chemistry are described,
including the transition metal ions reactivity emission, deposition processes and variable
photolysis in the aqueous phase [56]. In the present work, Compounds containing an
azomethine group (>C=N-), Schiff bases, are used for determination of the studied transition
metal ions. Schiff bases are generally bi or tri dentate ligands capable of forming very stable
complexes with transition metal ions. The wide use of antibiotics in man and animals and
their extensive use in areas other than the treatment and prophylaxis of disease have resulted
in a serious problem of drug resistance. Many of the well- known antibiotics, penicillin,
streptomycine, tetracycline ect; are chelating agents, their action is improved by the presence
of small amounts of metal ions. The antimicrobial activity of the ligands and their transition
metal complexes against different bacteria are also reported. Copper complexes have more
antibacterial activity against the bacteria staphyloccus aureus, klebsiella pneumonia
[216,579].
Schiff base can be used in dyestuff production, liquid crystal industries and also in
pharmacology. They are synthetic oxygen carriers and they have been produced from
intermediate products in enzymatic reactions and used as antitumor’s, therefore, it is very
important to prepare its transition metal complexes [510] Schiff bases are organic compounds
with great utility in important fields as: medicine agriculture, cosmetic products [511, 583].
Some Schiff bases present anticancer [512], antitumor [116], antibacterial [53,580]
activity; they play a prominent part in the enzymatic or unenzymatic transaminating reactions
of the carbonyl compounds with amino acids [542,513]. In the coordinate chemistry field, a
lot of Schiff bases operate as ligands [529, 584]. Some of the Schiff bases complex
combinations with metals are used as insecticides, fungicides, herbicides [546]. Can be
remarked the large field of the biological action presented by the Schiff bases derived from
aromatic 2-hydroxyaldehydes [543].
Schiff bases have a large number of synthetic uses in organic chemistry [585,586].
Acylation of Schiff bases by acid anhydrides, acid chlorides and acyl cyanides is initiated by
attack at the nitrogen atom and leads to net addition of the acylating agent to the carbon-
nitrogen double bond. Reactions of this type have been put to good use in natural product
synthesis.
Schiff bases appear to be an important intermediate in a number of enzymatic
reactions involving interaction of an enzyme with an amino or a carbonyl group of the
substrate. One of the most important types of catalytic mechanism is the biochemical process
32
which involves the condensation of a primary amine in an enzyme usually that of a lysine
residue, with a carbonyl group of the substrate to form an imines or Schiff base. Stereo
chemical investigation carried out with the aid of molecular model showed that Schiff base
formed between methylglyoxal and the amino group of the lysine side chains of proteins can
bent back in such a way towards the N atom of peptide groups that a charge transfer can
occur between these groups and oxygen atoms of the Schiff bases. In this respect pyridoxal
Schiff bases derived from pyridoxal and amino acids have been prepared and studied from
the biological point of view. Transition metal complexes of such ligands are important
enzyme models. The rapid development of these ligands resulted in an enhance research
activity in the field of coordination chemistry leading to very interesting conclusions.
The carbon-nitrogen double bond of Schiff bases like the carbon-oxygen double bond
is readily reduced by complex metal hydrides [530,525]. Reduction of this type is probably
the most efficient and convenient method for the conversion of C=N into amino compounds.
Thus lithium aluminium hydride in THF at room temperature (or in difficult cases at elevated
temperature) smoothly reduces Schiff bases in high yield (> 90 %) to secondary amines.
Sodium borohydride is an equally effective reducing agent and is preferred to lithium
aluminium hydride because of its inertness to a wider range of solvent media and because of
its greater specificity in that other substituents such as nitro or chloro reducible by lithium
aluminium hydride are unaffected by sodium borohydride. Reagent of this type is sodium
cyanoborohydride (NaBH3CN).
When heterocyclic compounds played an important role in regulating biological
activities. Many Schiff base metal complexes are known to be medicinally important and are
used to design medicinal compounds. Nitro and halo derivatives of Schiff bases are reported
to have antimicrobial and antitumor activities [562]. Antimicrobial and antifungal activities
of various Schiff bases have also been reported [563,582]. Fungi toxicity of some Schiff
bases have investigated by Sahu et al.[73]. Gawad et al. reported high antimicrobial activities
of some Schiff bases [533]. Many Schiff bases are known to be medicinally important and are
used to design medicinal compounds [551]. Cinnamldehyde is a well-established natural
antimicrobial compound. It is probable for cinnamaldehyde to react with amino acid forming
Schiff base adducts in real food system. The main advantage of cinnamaldehyde is that direct
contact is not required for being active as antimicrobial. Cinnamaldehyde has been shown to
be active against a range of food borne pathogents bacteria.
Wei et al. have prepared some adducts by the direct reaction of amino acids with
cinnamaldehyde at room temperature. Their antimicrobial activities were evaluated with
33
benzoic acid as a reference. Both cinnamaldehyde and their adducts were more active against
three microbial strains at low pH. They were more active than benzoic acid at the same
conditions, also [568]. Parekh and co-workers have synthesized Schiff bases derived from
4-aminobenzoic acid and cinnamaldehyde. They were screened as potential antibacterial
agents against a number of medically important bacterial strains [262]. They concluded that
different response of the synthesized Schiff bases arise because of their structural differences
and are also solvent dependent. Srikar et al. used p-dimethyl amino cinnamaldehyde to form
desired Schiff base, which used for quantitative estimation of Sparfloxacin in bulk and
pharmaceutical dosage forms [466].
The antibacterial activities of chitosan and the Schiff base derived from chitosan and
cinnamaldehyde were investigated by Xioa and co-workers [115]. The results indicate that
the antibacterial activity of the Schiff base is stronger than that of chitosan. It was found that
antibacterial activity increases with the increase of Schiff base concentration.
CORROSION INHIBITORS:
An interesting application of Schiff bases is their use as an effective corrosion
inhibitor which is based on their ability to spontaneously form a monolayer on the surface to
be protected [478]. Schiff bases have been found to posses more inhibitor efficiency than
their constituent carbonyls and amines [518]. The results indicated that these Schiff bases
inhibited the corrosion efficiently. Some authors have attributed these considerably stronger
inhibition efficiencies to the presence of unoccupied p*- orbitals in the Schiff base molecules,
which enable electron back donation from the metal d-orbitals and thereby stabilize the
existing metal-inhibitor bond, which is not possible with the constituent amines [574].
MISCELLANEOUS APPLICATIONS:
Interest due to their thermal stability similar to polyamides and their using as solid
stationary phase for gas chromatography [526], their semiconductor properties [552],
mechanical strength, electrochemical and nonlinear optical properties [564], and useful
catenation ligand, where the coordination polymeric Schiff bases are extensively studies
[519]
Schiff base polymers are produced by the polycondensation of diamines with various
dicarbonylcompounds [517]. Khuhawar et al. synthesized and characterized Schiff base
polymers derived from 4, 4’- methylenebis (cinnamaldehyde) with various diamines [575].
Due to various applications of silver(I) complexes, for example as reagents in organic and
inorganic synthesis[217] , in photography or electrochemical silver plating , and as free
radical scavengers in industrial processes [50], these complexes have received considerable
34
attention in recent years[522]. Limited work related to the silver (I) complexes with mixed
ligands.
Amirnasr et al. have synthesized and determined crystal structure of two mixed ligand
silver(I) complexes, [Ag(ca en = is a bidentate Schiff base that prepared from
cinnamaldehyde and ethylendiamine, and X= N and SCN [507] 1,3- diene) iron complexes
have found many useful applications in organic synthesis [508]. Although a large number of
these compounds have been reported and their activity investigated [539], less is known of
the corresponding heterodynes compounds. In such compounds, which may be regarded as
derived from the basic butadiene unit by the replacement of one or more of the carbon atoms
by the oxygen or nitrogen, the possibility arises that the lone pair of electrons of the
heteroatom is involved with the metal-ligand bond [126]. The 1-aza-1,3-butadienes and their
tricarbonyl complexes are readily available by condensation of cinnamaldehyde with the
corresponding arylamine followed by complexation with the ennacarbonyldi-iron. Jarrahpour
et al,. have synthesized the 1-(2-aminopyridine)-4-phenyl-1,3-diene and 1-(3-aminopyridine)-
4-phenyl-1,3-diene as heterodynes for iron carbonyl complexes[498] . Knölker et al. have
reported that (η1-aza-1,3-butadiene) tricarbonyliron complexes are highly efficient for the
transfer of the tricarbonyliron fragment [499] .
Cyclometallation reactions are well-established for many of the metals in the periodic
table, especially where the metallation has occurred at an aromatic carbon atom [534].
However examplesinvolving cyclometallation of sp-(1, 2, 4-triphenyl-1-aza-cyclohexadienyl)
Re(CO)3. The crystal structure and properties of copper (I) complexes with multidentate
ligands has a growing interest in recent years [527], for their potential applications in
metallosupramolecular assemblies [535], bioinorganic chemistry [503] and catalysis [524].
Morshedi et al. have designed and prepared tetradentate N donor Schiff base ligand with
using of cinnamaldehyde. They have studied the coordination chemistry of their copper (I)
complexes [565].
Khalaji and Welter react N, N'-bis(ß-phenyl-cinnamaldehyde)-1,2-diiminoethane
(Phca2en) with a mixture of CuI and AgNO3 to yields the mononuclear [Cu(Phca2en)2]
[AgI2] complex. The X-ray crystallography showed that this complex consists of a
[Cu(Phca2en)2]+ cation and a [AgI2]- anion. Phca2en acts as a bidentate ligand coordinating
via two N atoms. Bolz et al. prepared Schiff bases with multiple binding sites for
supramolecular assemblies by condensation of para- nitro- and para-N,N dimethylamino
cinnamaldehyde with 1,3-dimethyl- and 1-butyl-5-aminobarbituric acid [540]. The
investigation of keto-enol tautomorism of synthesized Schiff bases by FTIR spectroscopy
35
confirmed that in the solid state these compounds exist only in the enol form. In all sighted
species, the absorption of light by the cis – retinal Schiff base rhodospin results in the
cis – trans isomerization of its chromophore as an important step [528]. Under different
conditions, p-substtuted cinnamaldehyde undergo a variety of different photoprocesses
including cis – trans isomerization [523]. The photobehavior of rhodospin is dependent on
molecular environment [600-611]. Kanthimiathi and Dhathathreyan have studied the
photoreaction of monolayers synthesized Shiff bases drived from condensation reaction of
p-nitro cinnamaldehyde with ethylene diamine and o-phenylene diamine at air /water
interface [479].
36
Scope of the present work:
The literature survey reveals there are very few reports on the synthesis of Schiff base
as well as the preparation of corresponding metal complexes based on p-Toluic hydrazide and
different aldehydes and ketones. Therefore the author has proposed to take up the work based
on the synthesis of new Schiff bases as well as the preparation of metal complexes of
industrial importance and their characterization using different analytical techniques.
p-Toluic Hydrazide has several important applications in many fields of greater
interest mainly medicine, Pharmaceitical, Agriculture, Biological, Anti-Cancer, Anti-
tuberculosis etc. p-Toluic Hydrazide is used the photochemical synthesis of various organic
compounds. It is also used in the preparation of polymers.
Employing p-Toulic Hydrazide as a common amine, the author in the present
investigation prepared altogether new provided a new developed Schiff base ligands from
p-Toulic Hydrazide with 2-Hydroxy Benzophenone, 2,4-Dihydroxy Benzophenone,
2-Hydroxy Benzaldehyde, 4-Hydroxy 3-methoxy Benzaldehyde, 2,4,5-Trimethoxy
Benzaldehyde (Asaronaldehyde) and 3,4,5-Trimethoxy Benzaldehyde.
The Synthesized Schiff bases are
1) 2-Hydroxy benzophenone + p-Toluic Hydrazide (OHBPPTH)
2) 2,4-Dihdroxy Benzophenone + p-Toluic Hydrazide (DHBPPTH)
3) 2-Hydroxy benzaldehyde + p-Toluic Hydrazide (OHBAPTH)
4) 4-Hydroxy 3-methoxy benzaldehyde + p-Toluic Hydrazide (VPTH)
5) 2,4,5-Trimethoxy benzaldehyde + p-Toluic Hydrazide (2-TMBAPTH)
6) 3,4,5-Trimethoxy benzaldehyde + p-Toluic Hydrazide (3-TMBAPTH)
The structures of the prepared Schiff bases were confirmed by elemental and spectral
analysis. Several metal complexes of industrial importance were also prepared by using the
above prepared new Schiff base ligands. Their structural were also proposed using several
analytical techniques like IR, NMR, UV, ESR, TGA-DTA, VSM and Powder-XRD
spectrophotometry.The thermal stabilities and conductivity measurements were studied by
thermal analysis and conductometry. The anti-bacterial activities of the above ligand and the
37
complexes were also screened.
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