20

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

21

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

22

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

23

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

24

[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

25

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].

26

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

27

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

28

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

29

[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

30

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].

31

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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