bis-Hydrazine metal glycolates and chloroacetates: Synthesis, spectral, and thermal studies

Article abstract of DOI:10.1081/SIM-200030212

Octahedral bis-hydrazine metal glycolates and chloroacetates, [MX ₂(N₂H₄)₂]_n, where M = Co, Ni, or Zn for X = HOCH₂COO and M = Mn, Co, Ni, Zn, or Cd for X = ClCH₂COO have been pr

Full text of DOI:10.1081/SIM-200030212

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bis‐Hydrazine Metal
Glycolates and
Chloroacetates: Synthesis,
Spectral, and Thermal
Studies
B. N. Sivasankar a , J. R. Sharmila a & L.
Ragunath b
a Department of Chemistry , Government Arts
College , Udhagamandalam, The Nilgiris, 643
002, India
b Department of Chemistry , Sri Ramakrishna
Engineering College , Coimbatore, India
Published online: 16 Nov 2010.
To cite this article: B. N. Sivasankar , J. R. Sharmila & L. Ragunath (2004)
bis‐Hydrazine Metal Glycolates and Chloroacetates: Synthesis, Spectral, and
Thermal Studies, Synthesis and Reactivity in Inorganic and Metal-Organic
Chemistry, 34:10, 1787-1800, DOI: 10.1081/SIM-200030212
To link to this article: http://dx.doi.org/10.1081/SIM-200030212
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SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY
Vol. 34, No. 10, pp. 1787–1800, 2004
bis-Hydrazine Metal Glycolates and
Chloroacetates: Synthesis, Spectral, and
Thermal Studies
1
2
B. N. Sivasankar,1, J. R. Sharmila, and L. Ragunath
*
1Department of Chemistry, Government Arts College,
Udhagamandalam, The Nilgiris, India
2Department of Chemistry, Sri Ramakrishna Engineering College,
Coimbatore, India
ABSTRACT
Octahedral bis-hydrazine metal glycolates and chloroacetates,
[MX2(N2H4)2]n, where M ¼ Co, Ni, or Zn for X ¼ HOCH2COO and
M ¼ Mn, Co, Ni, Zn, or Cd for X ¼ ClCH2COO have been prepared
and characterised by chemical analyses, magnetic moments, electronic
and infrared spectra, and thermal analyses (TG, DTG, and DTA). Infrared
spectra show the presence of bridging bidentate (n(N–N) ¼ 970 cm21
)
hydrazines and monodentate carboxylate ions. The thermal studies indi-
cate that the glycolate complexes decompose at lower temperatures
(60–450 8C) than the chloroacetates which decompose in the temperature
range 100–600 8C. The x-ray powder diffraction lines imply that the
*
Correspondence: B. N. Sivasankar, Department of Chemistry, Government Arts
College, Udhagamandalam, The Nilgiris 643 002, India; E-mail: sivabickol@yahoo.com.
1787
DOI: 10.1081/SIM-200030212
0094-5714 (Print); 1532-2440 (Online)
www.dekker.com
Copyright # 2004 by Marcel Dekker, Inc.

1788
Sivasankar, Sharmila, and Ragunath
compounds in each series of complexes are isomorphous with each other.
However, there appears to be no similarity in the x-ray powder diffraction
pattern between the two series of complexes.
Key Words: bis-Hydrazine; X-ray powder diffraction; DTA curves;
Glycolates.
INTRODUCTION
Hydrazine is a versatile ligand and forms a wide variety of complexes
with various metal ions. The monodentate and bridging bidentate coordination
of the hydrazine molecule on complexation has been well documented in the
literature.[1] The emerging interest in these hydrazine complexes are mainly
due to their structure and thermal behaviour.
The bis-hydrazine complexes of transition metal ions with a variety of
inorganic anions are well emphasised in the literature.[2] However, the corres-
ponding compounds with carboxylate ions are scarce and only a few reports
are available on these bis-hydrazine metal carboxylates.[3–12] Further, the
hydrazine metal complexes of substituted acetic acids such as glycolic acid
and chloroacetic acid are not known, in spite of the large number of simple
metal glycolates and chloroacetates that have been studied in detail.[13]
Hence, in continuation of our earlier work on hydrazine metal carboxy-
lates,[7–12] this work has been undertaken to study the structure and thermal
reactivity of some new bis-hydrazine metal glycolates and chloroacetates.
Six-coordination around the metal ion has been tentatively proposed based
on the analytical, magnetic, spectral, and thermal studies.
RESULTS AND DISCUSSION
The bis-hydrazine metal glycolate and chloroacetate complexes were pre-
pared and the microanalyses of the complexes (Table 1) conform with the
desired composition. The general equation for the formation of the complexes
is represented as follows.
MðNO3Þ2 ꢀ 6H2O þ 2XH þ 2N2H4 ꢀ H2O ꢁ!MX2ðN2H4Þ2
þ 2HNO3 þ 8H2O
where M ¼ Co, Ni, or Zn for X ¼ HOCH2COO and M ¼ Mn, Co, Ni, Zn, or
Cd for X ¼ ClCH2COO.
Our attempt to prepare bis-hydrazine manganese and cadmium glycolates
was unsuccessful and always resulted in the recovery of the starting

bis-Hydrazine Complexes
1789

1790
Sivasankar, Sharmila, and Ragunath
compounds. In addition, the corresponding iron and copper complexes could
not be prepared with both glycolic and chloroacetic acids due to the precipitation
of hydroxide in the case of iron and the reduction of Cu(II) ion to copper metal.
Magnetic Moments and Electronic Spectra
The observed room temperature magnetic moments[14] of the manganese
and nickel complexes indicates their high-spin nature. As expected, the zinc
and cadmium complexes are diamagnetic.
The electronic absorption spectra[15] of the cobalt complexes show a band in
4
the region 19,230–20,620 cm21, which is characteristic of the 4T1g(F) ! T1g(P)
transition. Both nickel complexes show two bands in the regions 17,400–17,540
3
3
and 26,670–27,300 cm21 which are assigned to the A2g ! T1g(F) and
3
3A2g ! T1g(P) transitions, respectively. In addition to these, all complexes
show two bands in the region 29,300 and 33,310 cm21 for charge transfer
transitions. The magnetic moments coupled with electronic spectral data
clearly indicate the high-spin octahedral nature of all of these complexes. The
magnetic moments and electronic spectral data are summarised in Table 2.
Infrared Spectra
The infrared spectra of all of the complexes show bands in the region
3200–3300 cm21, which are assigned to N–H stretching frequencies of the
hydrazine moieties. However, for the glycolate complexes the O–H stretching
frequencies overlap with the N–H stretching frequencies of hydrazine, and,
hence, their individual assignments could not be made.
The nasy and nsym carboxylate stretchings of all the complexes are seen
in the regions 1600–1590 and 1380–1370 cm21, respectively, with a Dn of
ꢀ220 cm21 showing the unidentate coordination[16] of carboxylate ions.
The N–N stretching frequency of hydrazine moities are observed at
970–960 cm21 indicating their bridging bidentate nature.[1] In these com-
pounds the monodentate coordination of hydrazine is ruled out for which
the N–N stretching frequency normally is expected at 940–930 cm21
.
Thermal Decomposition
[Co(OOCCH2OH)2(N2H4)2]n
This complex decomposes exothermically in the temperature range
60–120 8C with the loss of one N2H4 molecule to give cobalt glycolate

bis-Hydrazine Complexes
1791
Table 2. Magnetic moments and electronic spectral data.
Magnetic
moment meff.
(B.M.)
Wavelength
(cm21
Assignments
(transitions)
Complex
)
4
[Co(OOCCH2OH)2(N2H4)2]n
19,230
20,450
4T1g(F) ! T1g(P) 5.10
29,300
33,300
Charge transfer
3
[Ni(OOCCH2OH)2(N2H4)2]n
17,540
26,670
3A2g ! T1g(F)
3.20
3
3A2g ! T1g(P)
29,300
33,300
Charge transfer
Charge transfer
[Zn(OOCCH2OH)2(N2H4)2]n
[Mn(OOCCH2Cl)2(N2H4)2]n
[Co(OOCCH2Cl)2(N2H4)2]n
29,300
33,300
Diamagnetic
5.90
29,300
33,300
Charge transfer
4
20,620
4T1g(F) ! T1g(P) 4.73
Charge transfer
29,300
33,300
3
[Ni(OOCCH2Cl)2(N2H4)2]n
17,400
27,300
3A2g ! T1g(F)
3.31
3
3A2g ! T1g(P)
29,300
33,300
Charge transfer
Charge transfer
Charge transfer
[Zn(OOCCH2Cl)2(N2H4)2]n
[Cd(OOCCH2Cl)2(N2H4)2]n
29,300
33,300
Diamagnetic
Diamagnetic
29,300
33,300
monohydrazinate as the intermediate. The DTA shows a peak at 140 8C cor-
responding to this stage. This intermediate further decomposes in the tempera-
ture range 120–250 8C to give CoO as the residue. The weight loss in TG is
also in accordance with the formation of CoO. DTA shows an exotherm at
230 8C for the second stage of decomposition.
[Ni(OOCCH2OH)2(N2H4)2]n
The nickel complex also decomposes in two stages similar to that of
cobalt complex to give NiO as the final product. DTA shows two exotherms
at 100 and 180 8C corresponding to the two stages.

1792
Sivasankar, Sharmila, and Ragunath
[Zn(OOCCH2OH)2(N2H4)2]n
In the case of the zinc complex, though the decomposition pattern is
similar to the above two complexes and the TG temperature range for the
first stage is almost the same as the intermediate formed, zinc glycolate
monohydrazinate gives ZnO only at 450 8C, which is higher when compared
to the decomposition of the cobalt and zinc glycolate monohydrazinates.
[M(OOCCH2Cl)2(N2H4)2]n (M ¼ Mn, Co, and Ni)
The bis-hydrazine manganese, cobalt, and nickel chloroacetates decom-
pose in two stages. In the first stage, loss of both hydrazine molecules takes
place in the temperature range 130–240 8C to give the respective metal
chloroacetates as intermediates. These intermediates further decompose to
give the respective metal oxides. The DTA curves show that both stages are
exothermic.
[M(OOCCH2Cl)2(N2H4)2]n (M ¼ Zn and Cd)
The chloroacetate complexes decompose similar to the above three
complexes. However, these two complexes decompose, comparatively, at
lower temperature than the manganese, cobalt, and nickel complexes.
All of the chloroacetate complexes decompose at relatively higher
temperatures than the corresponding glycolate and glycinate[11] complexes.
This may be due to the formation of metal chlorides during decomposition,
which are known to decompose at higher temperatures as it is seen in
the thermal decomposition of hydrazinium metal chlorides.[17] The thermal
degradation data of the complexes are summarised in Table 3. The final
oxides are confirmed by their chemical analyses and x-ray powder
diffractions.
X-Ray Powder Diffraction
X-ray powder diffraction patterns of the glycolate complexes show iso-
morphism among each other. Interestingly, it is observed that these diffraction
patterns are similar to those observed previously in the case of bis-hydrazine
metal glycinates.[11] This may be due to the isoelectronic nature of the glyco-
late and glycinate ions, both acting as unidentate ligands in the bis-hydrazine
complexes. Hence, the structure of the glycolate complexes are expected to be
similar to that of the glycinate complexes. The x-ray powder diffraction data
for the complexes are given in Table 4.

bis-Hydrazine Complexes
1793

1794
Sivasankar, Sharmila, and Ragunath
All of the chloroacetate complexes show superimposable x-ray powder
diffraction patterns indicating their isomorphism. Since, as evident from the
physico-chemical studies, the chloroacetate ions also behave as unidentate
ligands, the structure of the bis-hydrazine metal chloroacetate complexes
are expected to be similar to that of the bis-hydrazine metal glycolate and
bis-hydrazine metal glycinate complexes,[11] because in all the three cases
the carboxylate ions behave as a monodentate ligands through carboxylate
oxygen and hydrazine behaves as a bidentate bridging ligand. Hence the
substitution will not effect the structure significantly. However, the x-ray
diffraction patterns of the chloroacetate complexes are different from those
of the other two series. This may be attributed to the lower electronegativity
of chlorine as compared to oxygen and nitrogen in glycolate and glycinate
ions, respectively, and is less susceptible for hydrogen bond formation in
the crystal lattice. Based on spectral, thermal and x-ray powder diffraction
˚
Table 4. X-ray powder diffraction data (d-values in A).
[M(OOCCH2OH)2(N2H4)2]n
[M(OOCCH2Cl)2(N2H4)2]n
Co
Ni
Zn
Mn
Co
Ni
Zn
Cd
6.81
3.93
3.49
3.45
3.26
2.73
2.59
2.51
2.48
2.14
1.96
1.93
1.80
1.76
1.72
1.65
1.50
—
6.76
3.95
3.51
3.44
3.27
2.71
2.58
2.52
2.47
2.14
1.97
1.93
1.80
1.77
1.71
1.64
1.52
—
6.71
3.97
3.48
3.47
3.28
2.72
2.59
2.53
2.47
2.15
1.97
1.92
1.80
1.77
1.72
1.64
1.49
—
8.12
5.75
4.38
4.13
3.99
3.56
2.92
2.88
2.83
2.71
2.59
—
8.19
5.87
4.29
4.15
3.97
3.58
2.91
2.89
2.82
2.70
2.60
—
7.97
5.79
4.31
4.09
3.92
3.59
2.93
2.85
2.80
2.73
2.61
2.56
2.21
2.17
—
8.04
5.83
4.33
4.11
3.97
3.62
2.92
2.87
2.81
2.71
2.60
2.57
2.21
2.17
2.07
1.99
1.96
1.91
1.85
1.78
1.64
1.58
8.12
5.75
4.35
4.13
4.00
3.56
2.95
2.86
2.81
2.72
2.61
2.58
2.22
2.18
2.07
1.99
1.95
1.90
1.84
1.79
1.64
1.58
2.21
2.18
—
2.22
2.17
—
2.00
1.95
1.91
1.85
1.78
1.64
1.58
2.00
1.96
1.91
1.85
1.78
1.64
1.58
1.99
1.96
1.91
1.84
1.79
1.64
1.58
—
—
—
—
—
—

bis-Hydrazine Complexes
1795
studies the following polymeric structure (Fig. 1) has been tentatively
assigned for the complexes. The x-ray powder diffraction patterns for
bis-hydrazine nickel glycolate, glycinate, and chloroacetate are shown in
Figs. 2–4, respectively, as representative examples.
CONCLUSIONS
From the present investigations, the following general observations may
be made.
i. Both glycolate and chloroacetate complexes form bis-hydrazine
complexes.
ii. While manganese and cadmium form only chloroacetate complexes,
the cobalt, nickel, and zinc form both glycolate and chloroacetate
complexes. However, iron and copper form neither glycolate nor
choloroacetate complexes.
iii. Physico-chemical and spectral studies indicate that both glycolate
and chlroacetate ions act as unidentate ligands and hydrazine in
both series of complexes coordinates to the metal as a bidentate
ligand.
iv. The glycolate complexes decompose at lower temperatures than the
chloroacetate complexes.
v. Both series of complexes give the respective metal oxides as the
final products as expected.
Figure 1. Suggested structure of [MX2(N2H4)2]n. M ¼ Co, Ni, or Zn for X ¼
HOCH2COO and M ¼ Mn, Co, Ni, Zn, or Cd for X ¼ ClCH2COO.

1796
Sivasankar, Sharmila, and Ragunath
Figure 2. X-ray powder diffraction pattern of [Ni(OOCCH2OH)2(N2H4)2]n.
vi. All of the above studies indicate that the complexes are all of high-
spin octahedral geometry with two unidentate carboxylate ions and
two bidentate hydrazine moieties.
vii. The x-ray powder diffraction data indicate isomorphism within each
series, but not between the two series of complexes.
viii. Based on the above facts and earlier studies on bis-hydrazine
metal acetate complexes[18] a polymeric structure with octahedral
geometry around the metal has been tentatively assigned for the
complexes.
Figure 3. X-ray powder diffraction pattern of [Ni(OOCCH2NH2)2(N2H4)2]n.

bis-Hydrazine Complexes
1797
Figure 4. X-ray powder diffraction pattern of [Ni(OOCCH2CL)2(N2H4)2]n.
EXPERIMENTAL
Materials and Methods
All chemicals used were of AnalaR grade and solvents were distilled
before use. Hydrazine hydrate (99–100%) and glycolic acid (55%) were
used as received from Qualigens Chemicals. The metal glycolate hydrates
and metal chloroacetate hydrates were prepared by the reported methods.[13,19]
Preparation of bis-Hydrazine Metal Glycolates
The complexes [M(OOCCH2OH)2(N2H4)2]n, where M ¼ Co, Ni, or Zn,
were prepared by adding an excess of hydrazine hydrate (2 mL, 0.04 mol) to
finely powdered metal glycolate dihydrate (0.01 mol). The reaction was
instantaneous and exothermic. During the reaction, the water molecules
were replaced by hydrazine moities and a colour change was observed in
the case of the cobalt and nickel compounds. In the case of cobalt complex,
the colour changes from pink to rosy red and in the case of nickel, the
colour changes from light green to violet. After completion of the reaction
(15 min), the resulting solid product was filtered, washed several times with
ethanol to remove excess hydrazine, and then dried in air. The complexes
are stable in air and insoluble in water, alcohol, and diethyl ether.
We also made an attempt to prepare the above complexes by mixing
an aqueous solution (50 mL) containing a mixture of hydrazine hydrate

1798
Sivasankar, Sharmila, and Ragunath
(2 mL, 0.04 mol) and glycolic acid (2.76 mL, 0.02 mol) with an aqueous
solution (50 mL) of the respective metal nitrate hydrates (0.01 mol). This
method resulted in the precipitation of the respective tris-hydrazine metal gly-
colates.[8] When 0.03 mol of hydrazine hydrate is used in the above procedure
with 0.02 mol of glycolic acid and 0.01 mol of metal nitrate hydrates, the
complexes were not precipitated.
Preparation of bis-Hydrazine Metal Chloroacetates
The complexes [M(OOCCH2Cl)2(N2H4)2]n where M ¼ Mn, Co, Ni, Zn,
or Cd were prepared by mixing an aqueous solution (50 mL) containing a
mixture of hydrazine hydrate (2 mL, 0.04 mol) and chloroacetic acid (1.89 g,
0.02 mol) with an aqueous solution (50 mL) of the respective metal nitrate
hydrate (0.01 mol). The precipitate formed after 30–40 min at room tempera-
ture was filterated, washed with ethanol, and dried in air. The complexes are
stable in air except the cobalt and manganese complexes which undergo
partial decomposition on prolonged exposure to air. Hence, these two com-
plexes were stored in a vacuum desicator over P2O5. All these complexes
are also insoluble in water, alcohol, and diethyl ether.
The bis-hydrazine metal chloroacetates were also prepared by the method
followed for bis-hydrazine metal glycolates. However, from the analytical
data, it was observed that the purity of the samples prepared by this method
is less than when prepared by the previous method, where the complexes
were precipitated from the clear solutions.
Analyses
The metal contents of all the complexes were determined by EDTA
complexometric titration, after decomposing a known weight of the sample
with concentrated nitric acid. The hydrazine content was determined volume-
trically using 0.025 M KIO3 solution under Andrews’ condition.[20]
Physico-chemical Studies
The magnetic moments of the complexes at room temperature were
measured by Gouy’s method using [HgCo(CNS)4] as calibrant. Diamagnetic
corrections were estimated from Pascal’s constants. The electronic absorption
spectra of the complexes in Nujol mulls were recorded on a Shimdzu
UV-Visible 240 spectrophotometer. The infrared spectra of the complexes

bis-Hydrazine Complexes
1799
were recorded as KBr discs using a Perkin Elmer model 597 spectrophoto-
meter in the range 4000–400 cm21. The TG experiments were carried out
using a Perkin Elmer TGS 2 thermogravimetric system and a Dupont DTA
750 instrument was used to carry out differential thermal analysis. TG and
DTA experiments were performed in static air using platinum cups to hold
5–10 mg samples under ambient conditions. The complexes were heated up
to 600 8C and the heating rate employed was 10 8C/min. X-ray powder
diffraction patterns of the samples were recorded on a Philips PW 1050/70
diffractometer using CuKa radiation.
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Received November 12, 2002
Accepted June 13, 2004