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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
isonicotinoylhydrazone
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
2-Hydroxy-1-naphthaldehyde
isonicotinoylhydrazone
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
isonicotinoylhydrazone
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
isonicotinoylhydrazone
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
isonicotinoylhydrazone
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
2-Hydroxy-1-naphthaldehyde
isonicotinoylhydrazone
Th(IV), U(VI) 133
2-Hydroxy-1-naphthaldehyde
guanylhydrazone
Ce(IV) 134
1-[Di-(2-pyridyl)methylidene-5-
(salicylidene)thiocarbohydrazone
Zn(II) 135
3,4-Dihydroxybenzaldehyde
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
Pyridine-2-acetaldehyde
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
isonicotinoylhydrazone
U(VI) 157
2,4-Dihydroxyacetophenone
benzoylhydrazone
Mo(VI), V(V) 158
2,3-Dihydroxybenzaldehyde
isonicotinoylhydrazone,
3,4-dihydroxybenzaldehyde
isonicotinoylhydrazone and 2,3,4-
trihydroxybenzaldehyde
isonicotinoylhydrazone
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
Pyridine-2-acetaldehyde
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
isonicotinoylhydrazone
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
2,4-Dihydroxy benzaldehyde
isonicotinoylhydrazone
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
isonicotinoylhydrazone
Fe(II) 189
2,2’-Dipyridyl-2-pyridylhydrazone Pd(II) 190
2,4-Dihydroxy benzaldehyde
isonicotinoylhydrazone
Th(IV) 191
Pyridoxal isonicotinoylhydrazone Fe(II) 192
Pyridine-2-acetaldehyde
salicylhydrazone
Co(II) 193
2,2’-Dipyridyl-2-pyridylhydrazone Pd(II) 194
Pyridine-2-carboxaldehyde-2-
hydroxybenzoylhydrazone
U(VI) 195
2-Pyridylcarbaldehyde
isonicotinoylhydrazone
Fe(III) 196
2,2’-Dipyridyl-2-pyridylhydrazone Fe(II), Fe(III) 197
Di-2-pyridylketone salicyloylhydrazone Fe(II), Fe(III) 198
2-Hydroxy-1-naphthaldehyde
benzoylhydrazone
Cu(II), V(V) 199
Di-2-pyridylketone salicyloylhydrazon Zn(II) 200
Di-2-pyridylketone
isonicotinoylhydrazone
Fe(II) 201
Pyridine-2-carboxaldehyde
isonicotinoylhydrazone
Fe(II) 202
Di-2-pyridylketone
isonicotinoylhydrazone
Fe(II) 203
2-Hydroxyacetophenone
salicylhydrazone
Mg(II) 204
2-Hydroxy-1-naphthaldehyde
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
isonicotinoylhydrazone
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
2,4-Dihydroxy benzaldehyde
isonicotinoylhydrazone
Zn(II) 212
3,5-Dimethoxy-4-hydroxy-2-
aminoacetophenone
isonicotinoylhydrazone
Au(III) 213
O-vanillin furfuralhydrazone Os(VIII) 214
2,4-Dihydroxy benzaldehyde
isonicotinoylhydrazone
Ni(II) 215
Diacetylmonoxime-p-
hydroxybenzoylhydrazone
Sn(II) 216
2-Aminoacetophenone
isonicotinoylhydrazone
Pd(II) 217
Salicylaldehyde furfuralhydrazone Pt(IV) 218
14 | P a g e
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