chapter 1 a brief review on hydrazones as...

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Chapter 1

A Brief review on Hydrazones as analytical reagents

Hydrazones are azomethiens characterized by the presence of the triatomic group >C= N-

N<. These are distinguished from other members of this class such as imines, oximes etc.

by the presence of the two interlinked nitrogen atoms. The hydrazone group occurs in the

organic compounds of the following type.

N N

R

X Y

C

R

I

N N

R

X

C C

R'

X'II

Where

R and R’ = H, Alk, Ar, RCO, Ht (Heterocyclic group)

Y = H, Alk, Ar, RCO, Ht

X = H, Alk, Ar, Ht, Hal, OR”, SR-, CN, SO2R”, NO2, N=NR”, COOR”

The general name “Hydrazone” is used for all compounds having structure (I).The

compounds of type (II) are termed as “azines”.

Nomenclature

Hydrazones are usually named after the carbonyl compounds from which they are

derived. Thus, benzaldehyde and phenyl hydrazine give benzaldehydephenyl- hydrazone.

The name originally used was benzalidenephenylhydrazine .Some authors have recently

reverted to this system, which however is cumbersome when applied to more complex

hydrazones. The nomenclature widely used in literature is not in accordance with IUPAC

rules.

Many organic compounds react with metal ions and form colored precipitates or

solutions. Hence, they are extensively used as analytical reagents, even though it is

difficult to predict with certainity which organic compound is suitable for the analysis of a

particular metal ion. Yoe gave a list of more than twenty ways in which they are used. It

has been observed that the reactivity of organic reagents with metal ions in the use of the

former as analytical reagents requires the presence of certain acidic or basic groupings and

coordinating atoms.

The aim of research in this field is the discovery of compounds possessing a high

degree of selectivity and identification of the causes underlying such selectivity. While

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most of the reagents are not selective, various means are known where by the selectivity

of a reagent may be improved. These include adjustment of the pH, and the use of

masking agents which form complexes with the interfering elements in the determination

of the test ion. Within the organic reagent molecule, there is generally a single acidic or

basic group, or a combination of these two, which is the key to the reactivity of the

reagent.

Literature survey has revealed that organic compounds capable of forming chelates or

inner complex salts give better results than those containing only acidic or basic

groupings, in the field of inorganic analysis. The element in the organic molecule through

which the metal is bonded is generally oxygen or nitrogen, less usually it is sulphur. The

oxygen containing groups most often found in organic reagents are -OH, -CHO, -COOH,

>CO. The nitrogen containing groups (-NH2, =NH, heterocyclic N) met with in general

functional groups are amines (usually aliphatic), heterocyclic rings (usually pyridine),

oximes (in which bonding tends to be coordinated to the nitrogen instead of replacement

of hydrogen) and azo groupings. The aromatic orthohydroxy carbonyl compounds form

stable six membered rings with the metal ions. Hydroxy carbonyl compounds derived

from benzene and naphthalene, hydroxy quinones of naphthalene and anthracene series

have been reported as analytical reagents.

It is observed, that in many cases the formation of a precipitate or a soluble colored

product is dependent on the presence of definite atomic groupings. Such compounds are

therefore designated as metal binding groups with specific or selective action. But, it

cannot be over looked that the reaction conditions play a definite role in this direction.

Hence, proper choice of solvent and other factors are to be given greater importance.

Organic compounds can undergo extensive alteration in their structure as a result of

condensation and substitution reactions. These may bring in the useful changes in the

reagent to make them better organic reagents. A survey of literature shows, that organic

compounds containing a phenolic or enolic group and a coordinating group containing

nitrogen, oxygen or sulphur forms a variety of complexes with different metal ions.

It is found that -SH group of an organic compound exhibits a higher acidic character

than similarly bound –OH group. Thio-keto group (>C=S) also plays an important role

compared to its counterpart, keto group (>C=O).

It is observed that aromatic compounds containing nitroso (-N=O) as well as phenolic

– OH groups are also useful as analytical reagents. It is clear from the above brief review,

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that many organic compounds containing acidic or basic groups, besides the coordinating

groups form chelates easily and have been used extensively as analytical reagents.

However, these investigations reveal that sensitivity and selectivity of the reagent should

be established, even though general guidelines are available to predict the potentialities of

a reagent for the said purpose. In view of large and varied demand for the new methods to

determine the metal ions, under specific conditions, the search for new reagents is a

continuous process. This exercise of finding new and novel reagents as well as methods

for inorganic analysis has a special significance in these days in view of the alarming and

complex problem of environmental pollution.

Isonicotinoylhydrazones of carbonyl compounds act as good analytical reagents, but

they have not been fully exploited. Hence, in the present investigation a detailed study of

these reagents has been made with a view to find out their potentialities in inorganic

analysis. Hydrazones are usually named after the carbonyl compounds from which they

are obtained. Isonicotinoyl hydrazones are the condensation products of isonicotinic acid

hydrazide and the carbonyl compounds. These isonicotinoyl hydrazones are prepared by

refluxing a mixture of isonicotinicacidhydrazide and the desired carbonyl compound for 2-

3 h in slightly alkaline medium. The compound usually crystallizes out on cooling.

Many of physiologically active hydrazones find application in the treatment of

diseases like tuberculosis, leprosy and mental disorders. Hydrazones also act as

herbicides,

insecticides, nematocides, rodenticides and plant growth regulators.

Isonicotinicacidhydrazide (INH) is an important antitubercular agent and has potential

sites for formation of complexes with metal ions. It is also observed, that isonicotinoyl

hydrazones and their metal complexes possess higher activity and lower resistivity to

tuberculosis bacteria. These reagents, apart from those specified above are also potential

analytical reagents for the determination of several metal ions by different physico-

chemical techniques, of which the spectrophotometric determination occupies a special

place.

The analytical applications of hydrazones have reviewed by Singh and Katyal. A

review was published in this area in 1982. In this, the author reviewed the papers

published on analytical potentialities of hydrazones up to 1980. After 1980 so many

researchers have worked on the analytical potentialities of hydrazones. Hydrazones have

both analytical and biological applications, which attract so many researchers. Because of

so much of work published in this area, we are interested to review the papers published

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on analytical applications of hydrazones.

Preparation

Hydrazones are generally prepared by refluxing the stoichiometric amounts of the

appropriate hydrazine and a carbonyl compound of high purity dissolved in suitable

solvent. On cooling, the compound usually crystallizes out. Detailed account of their

preparation is given in a review.1

Non-analytical applications

Due to their physiological activity, many hydrazones like isonicotinoyl

hydrazones, aryl hydrazones find many applications. They are potential agents for

treatment of iron overload cancer2 and are also known for their antiproliferative effect

3.

Di-2-pyridyl ketoneisonicotinoylhydrazone and its analogues are capable of binding iron

to tridentate (N,N,O) ligands. These compounds are highly cytotoxic but show selective

activity against cancer cells. The interesting fact is their cytotoxicity is maintained even

after complexation with iron.4

Hydrazones are used in the treatment of diseases like

tuberculosis, leprosy and mental disorder. They are also used as plasticizers, stabilizers for

polymers and as polymerization initiators, antioxidants etc. They can act as rodenticides,

insecticides, herbicides, plant growth regulators and are intermediates in preparative

chemistry. Hydrazones are also used as plasticizers, stabilizers for the polymers and as

polymerization initiators, antioxidants etc. 3-N-methyl-N-(4-chloro-1-phthalazinyl)

and 3-N-methyl-N-(4-oxo-1-phthalazinyl) hydrazones possess anthelminitic activity.5

Hydrazone complexes are used in making rubber, as photographic materials6, as dyes for

wool and in industry. Hydrazones of 2-methyl pthalazone7 are effective sterilizers for

houseflies.

Analytical applications

Jain and Singh8 reviewed critically the applications of hydrazones as analytical

reagents. Hydrazone formation is extensively used in the detection, determination and

isolation of compounds containing the carbonyl group. Photometric methods for

determining aldehydes and ketones are based on their reaction with 2,4-

dinitrophenylhydrazine to form corresponding hydrazones.9,10

Bis

cyclohexanoneoxalyldihydrazone was one of the earliest used hydrazones for the

spectrophotometric determination of copper. With the traces of copper it gives a blue

colour and used for the determination of copper in human serum11

, plants12,13

, steel14,15

,

paper pulp products16

, non-ferrous metals and alloys17,18

and in cadmium sulphide.19

Some

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of the hydrazones employed as spectrophotometric reagents for the determination of metal

ions are listed in Table 1.0

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Table.1.0

List of Spectrophotometric determination of metal ions by using Hydrazones

Reagent Metal ion determined Ref

P-Dimethylamino benzaldehyde isonicotinoyl

hydrazone

Hg(II) 20

2-Hydroxy benzaldehyde isonicotinoyl hydrazone Al(III), Zn(II), Co(II),

Ni(II), Mn(II)

21

22

Pyridine-2-aldehyde-2-pyridylhydrazone (PAPH) Cu(II), Zn(II), Cd(II),

Fe(II), Ni(II), Mn(II),

Pd(II)

23,24

Picolinaldehyde-2-pyridylhydrazone Pd(II), Co(II) 25-28

2,2’-Bipyridyl-2-pyridylhydrazone (BPPH) Co(II), Fe(II), Zn(II),

Cd(II)

29-32

Naphthyl methyl ketone isonicotinoylhydrazone Ti(IV) 33

4-Hydroxy benzaldehyde isonicotinoylhydrazone V(V) 34

2-Hydroxy-1-naphthaldehyde

isonicotinoylhydrazone

Mo(VI) 35

Pyridine-2-aldehyde-2-quinolylhydrozone

(PAQH)

Co(II), Ni(II), Cu(II),

Fe(II), Pd(II)

36-41

2,2’-Pyridyl bishydrazone Fe(II), Cu(II), Co(II),

Ni(II)

42

Phenyl pyruvic acid quinolylhydrazone Cu(II) 43

Thiophene-2-aldehyde-2-benzothiazolylhydrazone Cu(II) 44

Anthranilicacid isopropylidine hydrazone V(V) 45

Salicylaldehyde isonicotinoylhydrazone Ga(III), In(III) 46

Salicylaldehyde benzoylhydrazone Cu(II) 47

5-Methyl furfural-2-benzothiazolylhydrazone Co(II) 48

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Reagent Metal ion

determined Ref

Furfural-2-benzo-thioazolylhydrazone Cu(II) 49

5-Chloro-2-hydroxy acetophenone


Mn(II) 50

6-Methyl picolinaldehyde quinoylhydrazone Pd(II) 51

5-Chloro-thiophene-2-aldehyde-2-

benzothiazolylhydrazone

Co(II), Cu(II) 52

Diacetylmonoxime p-Nitro phenylhydrazone Co(II) 53

Bisacetylazine hydrazone Cu(I) 54

Diacetyl-bis(2-pyridyl)hydrazone Co(II) 55



Fe(III), Fe(II), Al(III),

U(VI)

56-58

Benzothiazole-2-aldehyde quinolylhydrazone Cu(II), Pd(II) 59,60

Pyridoin phenylhydrazone Cu(II), Pd(II) 61,62

Pyridine-2-carboxaldehyde-2-hydroxy

benzoylhydrazone

Zn(II), V(V), Ni(II) 63-65

Bi(2-quinolyl ketone) pyridylhydrazone Pd(II) 66

2,2’-Bipyridyl quinolylhydrazone V(V), Zn(II), Co(II),

Pd(II), Rh(III),

Fe(III), Ni(II), Cu(II),

Cd(II), Hg(II)

67-71

Picolinaldehyde-4-nitrophenylhydrazone Pd(II) 72

Biacetyl(monohydrazone)quinolylhydrazone Co(II), Cu(II) 73

Benzil quinolylhydrazone Cu(II) 74

2,2’-Pyridyl bis-quinolylhydrazone Cu(II), Zn(II), Cd(II),

Rh(III), Hg(II),

Co(II), Pd(II)

75,76

Monohydrazone quinolylhydrazone Zn(II),Cd(II),Hg(II),

Rh(III), Pd(II), Fe(II),

Co(II), Ni(II)

77-81

2,2’-Bipyridyl-2-pyrimidylhydrazone V(V), Zn(II), Fe(II),

Ni(II), Cu(II), Cd(II),

Rh(III)

82-85

2,2’-Dipyridyl ketone hydrazone Cu(II), Hg(II) 86

6-Methyl-2-pyridaldehyde-2-quinolylhydrazone Cu(II) 87

Salicylaldehyde hydrazone Cu(II), Fe(III),Co(II),

Pd(II), Os(VIII)

88-90

Pyruvaldehyde-2-benzothiazolylhydrazone Cd(II) 91

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Reagent Metal ion

determined Ref

Benzil bis(2-hydroxy)benzoylhydrazone Ti(IV) 92

Di-2-pyridyl ketone-2-

furancarbothiohydrazone

Cu(II), Ni(II), Cd(II),

Fe(II), Re(VII)

93

Ortho hydroxy acetophenone


V(IV) 94

Bis(isonicotinoylhydrazone) Bi(III),Zr(IV) 95,96

Diphenylglyoxal bis(2-hydroxy

benzoylhydrazone)

Ca(II) 97

2,2’-Bipyridyl phenylhydrazone Pd(II) 98

Dibenzylidenethiocarbohydrazone Ru(III) 99

2,4-Dihydroxy acetophenone


Mo(VI), Al(III),

Ni(II),V(V), Hg(II),

Ag(I), Mn(II), Co(II)

100-103

2,2’-Dipyridyl-2-benzothiazolylhydrazone Fe(II) 104

2,2’-Bipyridyl-2-pyridylhydrazone Pd(II) 105

2-Pyridyl-3-sulphophenylmethanone-2-

pyrimidylhydrazone

Fe(II)

106

2-Aceto-1-naphthal-N-salicylhydrazone Mn(II) 107

Di-2-pyridyl ketone benzoylhydrazone Pd(II) 108

Thiazole-2-carbaldehyde-2-quinolylhydrazone Pd(II) 109

Biacetyl mono(2-pyridyl)hydrazone Zn(II) 110

1-(2-Pyridylmethylidene)-5-

Salicylidene)thiocarbohydrazone

Pd(II)

111

Di-2-pyridylketone benzoylhydrazone Fe(II) 112

Benzyl-2-pyridylketone-2-quinolylhydrazone Hg(II) 113

2,6-Diacetylpyridine bis(benzoylhydrazone) U(VI) 114

2-Thiophenaldehyde-2-pyridylhydrazone

Cu(II) 115

Pyridine-2-carboxaldehyde isonicotinoyl

hydrazone

Zn(II)

116

1,2-Cycolhexanedionebis benzoylhydrazone) Ti(IV) 117

2,2’-Pyridyl bis(2-quinolylhydrazone) Zn(II), Cd(II) 118

N-Cyanoacylacetaldehydehydrazone

Mo(VI) 119

2,6-Diacetylpyridine bis(benzylhydrazone)

and 2,6-diacetylpyridine bis(2-

hydroxybenzoyl)hydrazone

Fe(II), V(V) 120

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Reagent Metal ion

determined Ref

Salicylaldehyde guanylhydrazone Mn(II) 121

2(3-Sulfobenzoyl)pyridine

benzoylhydrazone

Fe(III) 122

2-Pyridine carbaldehyde 2-(5-

nitropyridyl)

hydrazone

Ni(II) 123

Di-2-pyridylmethanone-1-

phthalazinylhydrazone

Ni(II) 124

2-Oximinodimedone mono

Guanylhydrazone

Fe(III) 125

3,4-Dihydroxybenzaldehyde

guanylhydrazone

Mo(VI) 126

4-Dimethylaminobenzaldehyde


Sb(III) 127

2,6-Diactylpyridine bis(arylhydrazone) U(VI) 128

Di-2-pyridylmethanone-2-(5-nitro)

pyridylhydrazone

Pd(II) 129

Salicylaldehyde carbohydrazone Zn(II) 130

Di-2-pridylketone-2-furoylhydrazone Ga(III) 131

Di-2-pyridylketone-2-pyridylhydrazone Pd(II) 132



Th(IV), U(VI) 133


guanylhydrazone

Ce(IV) 134

1-[Di-(2-pyridyl)methylidene-5-

(salicylidene)thiocarbohydrazone

Zn(II) 135


guanylhydrazone

Fe(III), V(V) 136

Di-2-pyridylketone benzylhydrazone Fe(II), Fe(III) 137

3,5-Dichlorosalicylaldehyde-2-

benzothiazolylhydrazone

V(V) 138

1,2-Cyclohexanedione-2-oxime-1-

guanylhydrazone

Cu(II) 139

Salicylaldehyde carbohydrazone Ga(III), Al(III) 140

1-[Di-(2-pyridyl)methylidene-5-

(salicylidene) thiocarbohydrazone

Bi(III) 141

Salicylaldehyde-4-

aminobenzoylhydrazone

Ga(III) 142

2-Benzimidazolyl-3-

sulphophenylmethanone-5-nitro-2-

pyridylhydrazone

Co(II) 143

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Reagent Metal ion

determined

Ref

Phenyl-2-picolylketone-2-

pyridylhydrazone

Pd(II) 144

Pyridine-2-acetaldehyde

salicyloylhydrazone

Ni(II) 145

Disulfonated(2-benzimidazol)(phenyl)

methanone-5-nitro-2-pyridylhydrazone

Ni(II) 146

Bis(thiophene-2-

aldehyde)thiocarbohydrazone

Ru(III), Ir(III) 147

Isoniazid-P-diethylaminosalicylaldehyde

hydrazone

Fe(II) 148

Di-2-pyridylmethanone-2-(5-nitro)

Pyridylhydrazone

Fe(II) 149

N,N-Oxalyl-

bis(salicylaldehyde)hydrazone

Cu(II) 150


salicylhydrazone

Pd(II) 151

Di-2-pyridyl ketone thiophenylhydrazone U(VI) 152

Salicilaldehyde guanylhydrazone Fe(II) 153

Isoniazid-2-hydroxy benzaldehyde

hydrazone in cetyl trimethyl ammonium

bromide

Al(III) 154

2-Pyridine carbaldehyde-3,5-dinitro-2-

pyridylhydrazone

Ni(II) 155

2-Hydroxy acetophenone

benzoylhydrazone

Mo(VI) 156

o-Hydroxypropiophenone


U(VI) 157

2,4-Dihydroxyacetophenone

benzoylhydrazone

Mo(VI), V(V) 158


isonicotinoylhydrazone,

3,4-dihydroxybenzaldehyde

isonicotinoylhydrazone and 2,3,4-

trihydroxybenzaldehyde


Fe(II) 159

Glyoxal-bis-isonicotinoylhydrazone U(VI), Fe(III) 160

1-(Phenyl-2-pyridyl)carbylidene-5-

resorcylidenethiocarbohydrazone and 1-

(phenyl-2-pyridyl)carbylidine-5-

salicylidene thiocarbohydrazone

Ga(III) 161

2-Pyridylketone benzoylhydrazone Fe(II), Fe(III) 162

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Reagent Metal ion

determined Ref

2,2’-Dipyridylketone

pecolinoylhydrazone

Ni(II), Co(II), Fe(II) 163

5-Methyl salicylaldehyde

guanylhydrazone

Fe(III) 164

Isoniazid-p-diethylaminosalicylaldehyde

hydrazone

Fe(III) 165


salicyloylhydrazone

Pb(II) 166

5-Nitro-2-pyridinecarbaldehyde-5-nitro-

2-pyridylhydrazone

Ni(II) 167

5-Methyl salicylaldehyde

guanylhydrazone

Mn(II) 168

Di-2-pyridylketone benzylhydrazone Co(II) 169

5-Chloro salicylaldehyde

guanylhydrazone

Mn(II) 170

2,4-Dihydroxy acetophenone

benzoylhydrazone

V(V) 171

Pyridoxal-4-hydroxy benzoylhydrazone Zr(IV) 172

P-methyl isonitroso

acetophenonehydrazone

Co(II) 173

2,4-Dihydroxy benzaldehyde


Ti(IV) 174

2-Acetyl thiophene guanylhydrazone Pd(II) 175

5-Chlorosalicylaldehyde

guanylhydrazone

Pd(II) 176

Difurfuraldehyde thiocarbohydrazone Rh(III), Pd(II) 177

Di-2-pyridylketone benzylhydrazone Ni(II) 178

Salicylaldehyde benzoylhydrazone Ca(II), Mg(II) 179

2-Hydroxy naphthaldehyde

guanylhydrazone

Cu(II) 180

Salicylaldehyde benzoylhydrazone and

2-hydroxy-1-naphthaldehyde

benzoylhydrazone

Fe(II) 181

2-Hydroxy benzaldehyde-5-nitro-

pyridylhydrazone

Co(II) 182

Res-acetophenone guanylhydrazone Ag(I) 183

Res-acetophenone guanylhydrazone Ru(III) 184

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Reagent Metal ion

determined

Ref



Mo(VI) 185

2-Hydroxy acetophenone

benzoylhydrazone

V(V) 186

α-(-Benzimidazolyl)- α’, α”-(N-5-nitro-

2-pyridyl hydrazone)-toluene

Cu(II) 187

Di-2-pyridylketone benzoylhydrazone Ni(II) 188

2-Pyridylcarboxaldehyde


Fe(II) 189

2,2’-Dipyridyl-2-pyridylhydrazone Pd(II) 190



Th(IV) 191

Pyridoxal isonicotinoylhydrazone Fe(II) 192


salicylhydrazone

Co(II) 193

2,2’-Dipyridyl-2-pyridylhydrazone Pd(II) 194

Pyridine-2-carboxaldehyde-2-

hydroxybenzoylhydrazone

U(VI) 195

2-Pyridylcarbaldehyde


Fe(III) 196

2,2’-Dipyridyl-2-pyridylhydrazone Fe(II), Fe(III) 197

Di-2-pyridylketone salicyloylhydrazone Fe(II), Fe(III) 198


benzoylhydrazone

Cu(II), V(V) 199

Di-2-pyridylketone salicyloylhydrazon Zn(II) 200

Di-2-pyridylketone


Fe(II) 201

Pyridine-2-carboxaldehyde


Fe(II) 202

Di-2-pyridylketone


Fe(II) 203

2-Hydroxyacetophenone

salicylhydrazone

Mg(II) 204


benzoylhydrazone

V(V), Fe(III) 205

Salicylaldehyde furfuralhydrazone Pd(II) 206

Salicylaldehyde-3-

oxobutanoylhydrazone

Ni(II) 207

Beta-cyclodextrin-o-vanillin

furfuralhydrazone

Cd(II) 208

Di-2-pyridylketone


Fe(II) 209

O-vanillin furoylhydrazone Cd(II) 210

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Reagent Metal ion

determined

Ref

3-Methylbenzothiazolin-2-one

hydrazone

Josamycin(Drug) 211



Zn(II) 212

3,5-Dimethoxy-4-hydroxy-2-

aminoacetophenone


Au(III) 213

O-vanillin furfuralhydrazone Os(VIII) 214



Ni(II) 215

Diacetylmonoxime-p-

hydroxybenzoylhydrazone

Sn(II) 216

2-Aminoacetophenone


Pd(II) 217

Salicylaldehyde furfuralhydrazone Pt(IV) 218

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chapter 1 a brief review on hydrazones as...

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