International Journal of Medicine and

Pharmaceutical Science (IJMPS)

ISSN(P): 2250-0049; ISSN(E): 2321-0095
Vol. 5, Issue 6, Dec 2015, 43-52
TJPRC Pvt. Ltd.

SYNTHESIS AND CHARACTERISATION OF VARIOUS AROMATIC AND

HETEROCYCLIC DERIVATIVES OF 2-PYRAZINOYL HYDRAZIDE
RAVISH KUMAR CHAUHAN
Associate Professor, Department of Chemistry, Indira Gandhi National College, Ladwa, Kurukshetra, Haryana, India
ABSTRACT
The chelating ligands are used to prepare chelates with a number of metal ions.The chelting ligands of various
aldehydic derivatives possess hard donor sites which are capable of forming complex compounds with hard metals. 2Pyrazinoyl hydrazide acts as good chelating ligand for various metal ions. The derivatives of 2-pyrazinoyl hydrazide
with various aldehydes may be prepared which may be considered by analytical chemists for formation of chelates with
metal ions. These chelates may be tested for antibacterial, fungicidal, anti- inflammatory and analgesic activities
because the Mannich bases possess all these activities. Considering these observations here we have undertaken the
preparation of 2-pyrazinoyl hydrazide and its derivatives with various aromatic and heterocyclic aldehydes. The present
paper deals with the synthesis, purification and structure elucidation of derivatives of various aromatic and heterocyclic
aldehydes with 2-pyrazinoyl hydrazide which can be used as chelating ligands.

Received: Nov 20, 2015; Accepted: Nov 24, 2015; Published: Nov 28, 2015; Paper Id.: IJMPSDEC20156

INTRODUCTION

Original Article

KEYWORDS: 2-Pyrazinoyl Hydrazide (PAH), Ligand, Hard Metals, Chelates, Aldehydic Derivatives

The formation of a variety of ligands like thiosemicarbazones, semicarbazones, dithiocarbamates,

benzothiozolines etc. is very important in coordination and bioinorganic chemistry because the complex formed by
these ligands with a various metal ions possess wide applications due to their biological potential.(1) Much work is
required on these model complexes for understanding the behavior of more complex molecules.Salicyclic acid has
been suggested to be the simplest model for humic substances in natural waters(2) and a convenient ligand
substrate for biologically relevant tyrosine phenoxide and glutamic /aspartic carboxylate functions.(3) It can adopt
several bonding modes
manganese complexes.

(4)

(5)

and act as an effective agent for the synthesis of photoactive carboxylato polynuclear

Salicylates of different metal ions(6) have wide spread applications both as antiseptic and

medicinal agents(7). Incorporation of -dimine as second ligand in metal-salicylato frame increases the cytotoxicity
and the neutral molecules get easily transported across the cell membranes.(8) Here we have undertaken the
preparation of 2-pyrazinoyl hydrazide and its derivatives with various aromatic and heterocyclic aldehydes. The
complexing behaviour of these ligands with transition metal ions and lanthanide series ions will be helpful to
provide valuable information for better understanding about their biological importance.

MATERIALS AND METHODS

The Pyrazine-2-carboxylic acid hydrazide prepared beforehand according to published procedure. [Merck
F.E. Chem Abstr. 30 (1936) 6994] while substituted benzaldehydes were obtained from Johnson chemical
company. All other chemicals used were of AR grade. Solvents were purified and dried before use by usual

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44

Ravish Kumar Chauhan

procedures. The derivatives prepared were crystallized and their purity was ascertained by thin layer chromatographic
screening. The elemental analysis was carried out which helped to establish the structures of the compounds. The
molecular weight of the derivatives were determined which were in agreement to the theoretical values. The electronic
spectra were recorded on a schimadzu spectrophotometer and IR spectra (KBr/nujol) on a Perkin Elmer spectrophotometer.

SYNTHESIS AND CHARACTERISATION OF VARIOUS AROMATIC AND HETEROCYCLIC

DERIVATIVES OF 2-PYRAZINOYL HYDRAZIDE (PAH)
General Method of Synthesis
Ethanolic solution of 2-pyrazinoyl acid hydrazide (0.1 M) and aldehydes (0.1M) were mixed together in a round
bottom flask and refluxed for two hours on water bath. On cooling the contents solid comes out, which was filtered through
suction, washed with ethanol and ether, and dried over anhydrous calcium chloride, finally recrystallised from ethanol. The
various derivatives were synthesized as below.

Benzy1lidene-2-Pyrazinoyl hydrazone (C12H10N4O): On mixing required amount of benzaldehyde and 2pyrazinoyl hydrazone in equivalent ratio in ethanol, was subjected to general method of synthesis. Colourless
crystalline compound was obtained (65% yield) having m.p. 140C. The molecular weight was determined by
osmometric method using benzil as reference.
The derivative is freely soluble in DMSO, DMF, acetone, acetonitrile, dioxane but insoluble in water, benzene

and diethyl ether.

Anisalidene-2-pyrazinoyl hydrazone (C13H12N4O2): On mixing equivalent amount of anisaldehyde and 2pyrazine carboxylic acid hydrazide (1:1) in ethanol, 0.1 mol. each in a round bottom flask was subjected to
general method of synthesis. Shining colourless crystalline compound was obtained (Yield 70%) with m.p. 150C.
The molecular weight was determined by osmometric method using benzil as reference.
The compound is freely soluble in DMSO, DMF, dioxane, acetonitrile, acetone and benzaIdehyde, slightly soluble

in isopropyl alcohol, chloroform and insoluble in water and benzene.

4-Hydroxy-3-methoxy benzylidene-2-pyrazinoyl hydrazone (C13H12N4O3): A solution of 3-methoxy-4hydroxy benzaldehyde (5.0 m mole) was added to pyrazine-2-carboxylic acid hydrazone (5.0 m mole) in dry
ethanol (20 ml). The reaction mixture was refluxed on water bath for one hour resulting in the formation of yellow
solid (yield 16%) having m.p. 200C. Molecular weight was determined by the usual method.
The compound is freely soluble in DMSO, DMF, dioxane, and acetone, slightly soluble in nitrobenzene and

insoluble in water, benzene, diethyl either.

p - (N, N - diethylamino) benzy1lidene2-pyrazinoyl hydrazone (C16H19N5O): To a solution of 2-pyrazinoyl

hydrazide (4.0 m mole) in about 20 ml of ethanol, equivalent (4.0 m mole) of p-(N,N-diethyl amino)
benzaldehyde (10 ml) was added dropwise. Reaction mixture was refluxed on water bath for one hour. On
concentration and cooling yellow solid separated out. It was filtered and subjected to usual procedure. M.P. 140C
yield (70%).
The compound is freely soluble in methanol, ethanol, dioxane acetone, DMF, DMSO and acetonitrile, and

insoluble in water, benzene and diethyl ether.

Impact Factor (JCC): 5.4638

NAAS Rating: 3.54

45

Synthesis and Characterisation of Various Aromatic and Heterocyclic Derivatives of 2-Pyrazinoyl Hydrazide

Cinnamalidene-2-pyrazinoyl hydrazone (C14H12N4O): To a solution of pyrazinoyl-2-acid hydrazide (0.1mole)

in ethanol was added cinnamaldehyde in equivalent amount in 20 ml ethanol. The reaction mixture was refluxed
on water bath for about one hour. After completion of the reaction, colourless mass appeared in good amount
(yield 70%), which was filtered, washed, dried and crystallized. The m.p. of the product was 165C. Its molecular
weight was determined by osmometric method.
The compound is freely soluble in methanol, ethanol, dioxane, onitrile, DMF and DMSO, insoluble in water,

benzene, xylene and chloroform.

4-Methyl

salicylidene-2-pyrazinoyl

hydrazone

(Vanillin)

(C13H12N4O2):

solution

of

4-methyl-

salicylaldehyde (10.0 m mole) in the appropriate solvent ethanol (10 ml) was taken in a round bottom flask
equipped with a reflux condenser. To the refluxing solution of the aldehyde, the 2-pyrazinoyl hydrazide solution
(10.0 m mole) was added drop wise and the refluxing continued for 45 minutes during which time the reaction
mixture becomes yellow. The solvent was then removed in vacuo. The residue obtained after the removal of the
solvent by distillation was crystallized with ethanol. Yield 75%, M.P. 175C. Its molecular weight was
determined osmometric method using benzil as reference.
The compound is freely soluble in DMSO, DMF, acetonitrile, ethanol and acetone but insoluble in water,
chloroform and benzene.

2-Furfuralidene-2- pyrazinoyl hydrazone ((C11H10N4O2): A solution of 2-furfuraldehyde (4.0 m mole) in 20

ml of ethanol containing 2-pyrazinoyl hydrazide (20 ml) in equivalent amount was refluxed on water bath for one
hour. After completion of the reaction, the product was filtered. The crude product was crystallized with ethanol
and dried over anhydrous sodium sulphate. M.P. 1750C, yield 70%.

RESULTS AND DISSCUSSIONS

Analytical and chemical data: The elemental analysis and molecular weight of Pyrazine-2-carboxylic acid
hydrazide and its hydrazones with different aldehydes were calculated (Table 1). All these compounds contain
carbon, hydrogen, oxygen and nitrogen. Results show that the percentage composition of various elements in
these compounds is nearly same to the theoretical values. Similarly the molecular weights determined
experimentally are quite close to the theoretical values. Slight variations in percentage composition of elements or
molecular weights of the derivatives may be due to experimental error.
Table 1: Analytical and Chemical Data of 2-Pyrazinoyl
Acid Hydrazide and its Derivatives with Various Aldehydes
S.
No.

Compounds

1.

PAH - (C5H6N4O)

2.

PAH-Benzaldehyde (C12H10N4O)

3.
4.
5.

PAH- Anisaldehyde
(C13H12N4O2)
PAH Vanillin
(C13H12 N4O3)
PAHP-(N,N-diethylamino
benzaldehyde (C16H19N5O)

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Mol.wt.
Found
(Calcd.)
132.60
(138)
222.00
(226)
248.80
(256)
265.83
(272)
290.12
(297)

m.p.0
C

Abbreviation
used

165

PAH

140

PAH-BENZ

150

PAH-ANSL

200

PAH-VANI

140

PAH-PDEAB

% Chemical Analysis Found

(Calcd)
C
H
N
43.40
4.27
40.48
(43.47)
(4.34)
(40.57)
63.50
4.34
24.70
(63.71)
(4.42)
(24.77)
60.85
4.60
21.80
(60.93)
(4.68)
(21.87)
57.28
4.35
20.50
(57.35)
(4.41)
(20.58)
64.57
6.30
23.45
(64.64)
(6.39)
(23.56)
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Ravish Kumar Chauhan

Table 1: Contd.,
6.
7.
8.

PAH Cinnamaldehyde
(C14H12N4O)
PAH4-Me-Salicylaldehyde
(C13H12N4O2)
PAH Furfuraldehyde
(C11H10N4O2)

248.74
(252)
250.00
(256)
225.70
(230)

165

PAH-CAH

175

PAH-MSALI

175

PAH-Fural

64.64
(66.66)
60.82
(60.93)
57.32
(57.39)

4.64
(4.76)
4.58
(4.68)
4.25
(4.34)

22.15
(22.22)
21.77
(21.87)
24.24
(24.34)

Thin Layer Chromatographic Screening: Pyrazine-2-carboxylic acid hydrazide and its hydrazones with
different aldehydes were screened for thin layer chromatography, using different mobile phases. Clear single spot
of pyrazine-2-carboxylic acid hydrazide and hydrazones were observed. No spot corresponding to the spot of
pyrazine-2-carboxylic acid hydrazide was observed with any of the hydrazones, indicating absolute purity of the
hydrazones Rf -value of different compounds with different solvents are summarized in table 1. Increase in Rf value with different solvent systems is in the order T2 < T6< T5 < T4 < T3 < T1 and this indicates that Rf -value
increases with increase in the polarity of the solvent system. Rf-value is minimum (2.0 -- 5.1) with acetic acid
(glacial) : benzene (1:9) and maximum (93.00) with methanol : ammonia solution, strong (100:1.5).

Table 2: Thin-Layer Chromatographic Behaviour of Derivatives using T1 Methanol: Ammonia Solution Strong
(100:1.5) T2 Acetic acid Glacial: Benzene (1:9), T3 Ammonia Solution, Strong: Ethanol (90 Percent): Dioxane
(5:60:35), T4 Acetic acid Glacial: Ethanol (90%): Water (30 : 60 : 10), T5 - n- Butyl Alcohol: Methanol (40:60) and
T6 Ammonia Solution, Strong : Benzene: Dioxane : Ethanol (90%) (5:50:40:5) as Mobile Phase
Rf x 100
S.No.

PAH-derivative of...

1
1.
2.
3.
4

2
Nil (C5H6N4O)
Benzaldehyde (C12H10N4O)
Anisaldehyde (C13H12N4O2)
Vanillin (C13H12N4O3)

p-Diethylaminobenzaldehyde
(C16H19N5O)

6
7
8.

Solvent
System
I
3
85.0
93.0
93.0
92.0

Solvent
System
II
4
4.0
5.1
3.2
2.0

Solvent
System
III
5
60.5
67.2
66.0
59.0

Solvent
System
IV
6
52.6
64.4
61.2
59.8

Solvent
System
V
7
38.2
55.4
52.0
53.2

Solvent
System
VI
8
18.0
48.5
45.7
8.6

93.0

2.5

70.3

54.0

57.5

46.4

86.5

4.1

70.8

64.7

52.0

47.4

72.0

4.1

60.3

62.0

52.5

10.2

84.0

3.7

65.4

61.3

45.4

32.3

Cinnamaldehyde
(C14H12N4O)
4-Me- Salicylaldehyde
(C13H12N4O2)
Furfuraldehyde (C11H10N4O2)

Silica gel G (incorporating 13% calcium sulphate as binder) was used as absorbent

The spots were detected by iodine vapours.

Impact Factor (JCC): 5.4638

NAAS Rating: 3.54

Synthesis and Characterisation of Various Aromatic and Heterocyclic Derivatives of 2-Pyrazinoyl Hydrazide

47

Figure 1: I. R. Spectra of Organic Compounds

Figure 2: I.R. Spectra of Organic Compounds

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48

Ravish Kumar Chauhan

Table 3a: Ultra Violet and Infra Red Frequencies (cm-1) and their Tentative Assignment
of Pyrazine-2 Carboxylic Acid Hydrazide (PAH) and its Aldehydic Derivatives
PAH
(C5H6N4O)
1

39216
(255.0 nm)
0.406
3320vs
3210vs
3020vs
2950sh
2850sh
--1670vs
1650sh
1600vs

1570sh
1540ms

PAH-BENZ
(C12H10N4O)

PAH-ANSL
(C13H12N4O2)

PAH-VANI
(C13H12N4O3)

Tentative
Assignment

2
3
4
UItraviolet absorption in cm-1 & nm (nanometer)
and maximum values () (conc. 10 mcg/ml)
34483
33333
30769
(290.0 nm)
(300.0 nm)
(235 nm)
0.964
1.026
0.903
Infra-red Frequencies (cm-1)
3270vs
3500vs
3280vs
3200s
3400vs
(NH)
3070b
3040b
3200s
Intramolecular
2995b
3100ms
H-bonding vis2910s
2950s
-vis keto-enol
2840s
isomerism
--2650s
2610ms
(O-CH3)
1660vs
Amide band I
1650vs
1660vs
1640sh
(C=O)
Amide band II
1605s
1600vs
(-CH=N) of
1605vs
1590ms
1580sh
immine and NH
bending
Antisymmetric
or symmetric
1550ms
1560sh
1550vs
vibrations
1510ms
1505vs
(C=C)+(C=N)
of pyrazine ring.

Table 3b: Ultra Violet and Infra Red Frequencies (cm-1) and their Tentative Assignment
of Pyrazine-2 Carboxylic acid Hydrazide (PAH) and its Aldehydic Derivatives
PAH
(C5H6N4O)

PAH-BENZ
(C12H10N4O)

PAH-ANSL
(C13H12N4O2)

PAH-VANI
(C13H12N4O3)

1475s
1420s

1480ms
1450ms
1420vs

1340vs

1360vs
1340vs

1205vs

1210s

1105ms

1180s
1160ms
1135ms

1030vs

1090b
1070ms
1030vs

---880vs
Impact Factor (JCC): 5.4638

985s
960vs
920vs
880s

1490sh
1460sh
1420vs
1355ms
1340sh
1310vs
1290sh
1250vs
1200b
1175vs
1160vs
1120s
1070vs
1040vs
960ms
920ms
885vs

1470vs
1450s
1420vs
1380vs
1300ms
1290ms
1250s
1220sh
1190ms
1160ms
1120vs
1080b
1060ms
1020vs
950sh
940vs
930s
900vs

Tentative
Assignment

C-H
bending
modes of benzene
ring and hetero
ring.
Amide band III
(C=O) + (CN)
+ (CO) + (CN)
C-H
in-plane
deformation
Amide band IV
(NCO) + (CO)
Pyrazine
ring
breathing modes
and NH rocking
modes.
Pyrazine
deformation

ring

(N-N)
NAAS Rating: 3.54

49

Synthesis and Characterisation of Various Aromatic and Heterocyclic Derivatives of 2-Pyrazinoyl Hydrazide

Table 3b: Contd.,

825vs

700vs
680b
620s

835s
760vs
740ms

830vs
810vs
775s

700vs

720ms
700ms
640b

860vs
820vs
790b
740s
700vs
650b
620s
580b

In- plane pyrazine

ring deformation
and (NH) out of
plane deformation.

s- sharp, ms- medium sharp, vs-very sharp, sh-shoulder, b-broad, vb-very broad
Table 4a: Ultra Violet and Infra Red Frequencies (cm-1) and their Tentative Assignment
of Pyrazine-2-Carboxylic Acid Hydrazide (PAH) and its Aldehydic Derivatives
PAH- PDEAB
(C16H19N5O)
5

27778
(360.0 nm
0.986)
3400vs
3200s
3000s
----1660s
1640sh

PAH-CAH
PAH-MSALI
PAH-Fural
Tentative Assignment
(C14H12N4O) (C13H12N4O2) (C11H10N4O2)
6
7
8
UItraviolet absorption in cm-1 & nm (nanometer)
and maximum values () (conc. 10 mcg/ml)
35714
31250
32258
(280.0 nm)
(310.0 nm)
(310.0 nm)
1.206
1.022
1.022
Infrared frequencies
3410vs
3200s
3450b
3140sh
3100s
3150b
(NH)
3000s
3050s
Intra molecular H2850sh
3000b
2950s
bonding vis-a-vis
keto-enol isomerism.
----------- (O-CH3)
Amide band I
1660vs
1680s
1640s
(C=O)
1640sh
1640s

1600vs

1620sh
1590s

1620s
1600s

1620s

1520s

1575sh
1560ms

1580b
1500s

1550vb

1420b

1495s
1475s
1465vs

1480s
1420s

1480ms
1410s

Amide band II
(CH=N) of immine N
and NH bending.
Antisymmetric or
symmetric vibrations
(C=C)+ (C=N) of
pyrazine ring.
C-H bending modes of
benzene ring and hetero
ring.

Table 4b: Ultra Violet and Infra Red Frequencies (cm-1) and their Tentative Assignment of
Pyrazine-2- Carboxylic Acid Hydrazide (PAH) and its Aldehydic Derivatives

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PAH- PDEAB
(C16H19N5O)
5
1360vs

PAH-CAH
(C14H12N4O)
6
1360vs
1300vs

PAH-MSALI
(C13H12N4O2)
7
1360vs
1330sh
1300vs

PAH-Fural
(C11H10N4O2)
8
1390s
1330s

1290ms
1220s

1195s

1275s
1200ms

1180ms
1140s
1120s

1180s
1140s
1120s

1280b
1240s
1220s
1190s
1150vs
1110s

1150s
1120b

Tentative
Assignment
Amide band III
(C=0)+
(CN)+ (CO) +
(CN)
C-H in-plane
deformation
Amide band IV
(NCO) +
(CO)
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Ravish Kumar Chauhan

Table 4b: Contd.,

1050s
1020s

1060ms
1025vs

1070s
1020s

1080sh
1060vs
1020ms

980s
940s
910s
810vs

970vs

980ms
920ms
880vs
820s
760vs

940vs

700vb

900vs
830sh
820s
740vs
720s
700s
620s

720ms

900ms
880ms
820vs
740vs
700vs
620s
590vs

Pyrazine ring
breathing modes
and NH rocking
modes.
Pyrazine ring
deformation.
(N-N)

In-plane pyrazine
ring deformation
and (NH) out of
lane deformation

s-sharp, ms-medium sharp, vs-very sharp, sh-shoulder, b-broad, vb-very broad

Infrared Spectral Studies: The infrared spectral data of pyrazine-2-carboxylic acid hydrazide and its various
derivatives with benzaldehyde(PAH-BENZ), anisaldehyde (PAH-ANSL), vanillin (4-hydroxy-3-methoxy
benzaldehyde)(PAH-VANI), p-(N,N-diethylamino) benzaldehyde (PAH-PDEAB), cinnamaldehyde (PAH-CAH),
salicylaldehyde (PAH-MSALI), furfuraldeyde (PAH-Fural) are discussed in following sub sections.

Frequencies due to (NH) and intra molecular hydrogen bonding: All the compounds synthesized show
medium sharp and broad bands with a double structure in the range 3400-3000 cm-1 assigned to (NH) vibrations,
another medium broad band observed in region 3100-2840 cm-1 indicates strong intramolecular hydrogen bonding
in the molecule, resulting in the lowering of (OH) vibrations(9) From I.R. spectra of these compounds, (NH)
rocking modes are also observed as medium sharp bands in the region 1090-1020 cm-1, while (NH) out of the
plane deformation are observed as medium sharp band in the region 720-580 cm-1(10).

Frequencies due to amide band I, II & III: The sharp absorption from the compounds observed in the region
1680-1640 cm-1, 1620-1580 cm-1, 1390-1300 cm-1 and 1190-1105 cm-1 are assigned(11) to amide band I : (C=O),
amide band II : (CH=N) of immine-N and NH bending modes, amide band III : [ (C=O) + (C=N)+ (CO) +
(CN)] and amide band IV: [(NCO)] + (C-O)] respectively.
These bands indicate that the ligands primarily exist in the keto from in the solid state. Sharp absorption due to

amide band IV [ (N-CO) + (C-O)] observed in the region 1190-1105 cm-1 also confirms the existence of pyrazine-2carboxylic acid hydrazide and its various derivatives in the keto from in the solid state.(12)
o

Frequencies due to pyrazine ring of pyrazine-2-carboxylic acid hydrazide: The sharp absorption band due to
symmetric and antisymmetric (C=C) and (C=N) of pyrazine observed as sharp absorption band in the region
1580-1505 cm-1 are also found to be interfered by the sharp absorptions due to amide-II. The double bond
character of both these vibrations is considered to be increased due to the donation of electrons by the nitrogen
atom of the pyrazine ring. (13,14)
The pyrazine ring breathings modes are observed in all the ligands in the region 1090-1020 cm-1, out of plane,

pyrazine ring deformations are observed as a medium sharp absorption in the region 985- 920 cm-1, while in-plane pyrazine
ring deformation are observed in the region 720-500 cm-1 as sharp absorption bands.
o

Frequencies due to aldehydic adduct: The sharp absorption due to (O-CH3)) are observed in the region 26502620 cm-1 as well as 1090-1020 cm-1 in the IR spectra of pyrazine carboxylic acid hydrazide. (CH) bending modes

Impact Factor (JCC): 5.4638

NAAS Rating: 3.54

51

Synthesis and Characterisation of Various Aromatic and Heterocyclic Derivatives of 2-Pyrazinoyl Hydrazide

and (CH) in-plane deformations due to benzene ring as well as pyrazine ring observed in the region 1495-1410
cm-1 and 1290-1200 cm-1 respectively.
In the IR spectra of 2-furfuralidene-2'--pyrazinol hydrazone sharp band observed at 620cm-1 and 590 cm-1 are
tentatively assigned to furan ring deformations in the infrared spectra of free ligand. Very sharp and broad absorptions
observed at 3500 cm-1 and 3450 cm-1 respectively (15-19) are assigned to (OH).

CONCLUSIONS
The present study was concluded that along with the ligands having hard donor sites, the ligands with soft sites
may be synthesized which can coordinate with soft metals to form complexes. Simultaneously ligands having both hard
and soft donor sites may be prepared which can be used to form a variety of complexes with the metal ions.
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1.

Haidue I. Coord. Chem. Rev; 99 (1990) 253.

2.

Maeda M. Muratay and Ito K. j. Chem. Soc. Dalton Trans. (1987) 1833; Flaig W.
components edited by Gleseking J.E. (Springer

Benteispacher H. and Rietz E. Soil

Verlag, New Yrok) (1975) Vol. I. P-I.

3.

Vicent J.B., Floting K., Huffman J.C. and Christou G. Inorg. Chem; (1986) 25, 996.

4.

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