J. Iran. Chem. Soc., Vol. 8, No. 2, June 2011, pp. 477-483.

JOURNAL OF THE
Iranian
Chemical Society

Some New Organotin(IV) Schiff Base Adducts:

Synthesis, Spectroscopic Characterization and Thermal Studies
T. Sedaghat* and M. Monajjemzadeh
Department of Chemistry, College of Science, Shahid Chamran University, Ahvaz, Iran

(Received 26 June 2010, Accepted 4 October 2010)

Three new Schiff base adducts, [SnMe2Cl2(H2cdnaphen)] (1), [SnPh2Cl2(H2cdnaphen)2].C6H6 (2) and
[SnBu2Cl2(H2cdnaphen)2] (3) were synthesized by the reaction of SnR2Cl2 (R = Me, Bu and Ph) with a Schiff base ligand, Methyl
2-[2-(2-hydroxynaphthaldimino)ethylamino]-1-cyclopentene-1-dithiocarboxylate (H2cdnaphen). The new products were
characterized by elemental analysis, IR, 1H NMR and 119Sn NMR spectroscopies. Spectroscopic data suggest that H2cdnaphen
exists predominately in keto-amine tautomeric form and in all complexes acts as a monodentate neutral ligand coordinating with
the metal through oxygen atom, while the sulfur atom and imine nitrogen are not involved in coordination with the tin. Thermal
decomposition of the complexes was studied through thermogravimetry and the thermodynamic activation parameters were
determined by the Coats-Redfern method.

Keywords: Organotin(IV), Schiff base, Tautomeric forms, Thermal analysis, 119Sn NMR

INTRODUCTION a lot of work has been done on organotin(IV) complexes with

The chemistry of organotins has received considerable
attention during the past decades owing to their industrial,
agricultural and medicinal applications and their structural
variety. The organotin(IV) halides have a marked tendency to
increase their coordination number and are convenient systems
for the investigation of Lewis acid-base interactions. They
have demonstrated a wide variety of coordination geometries
around the Sn atom with a number of O-, N- and S- donors
and have a variety of structures and applications depending on
the number, type and arrangement of ligands about the tin
center [1-5]. To date, considerable efforts have been made to
synthesize and characterize organotin compounds of ligands
having heterodonor atoms (O, N, S) and many studies have
focused on structure-activity correlations [6-9]. More recently,
*Corresponding author. E-mail: tsedaghat@scu.ac.ir
Schiff bases due to their special pharmacological and
antitumor activity and their interesting variety of structural
possibility due to the multidenticity of these ligands [10-15].
Schiff bases are a class of favorite compounds in biological
field and play an important role in coordination chemistry
[16]. Both aliphatic and aromatic Schiff bases in their neutral
and deprotonated forms have been used to react with
organotin(IV) halides; the complexes formed exhibit variable
stoichiometry in the metal to ligand ratio and different modes
of coordination [17-25].
In continuation of our previous studies on organotin(IV)
complexes of Schiff bases [21-25], we report here the
synthesis, spectroscopic characterization and thermal analysis
of new organotin(IV) adducts with a potentially O-, N-, S-
donor ligand. Despite the recent increasing interest in
thermogravimetric analysis for predicting thermal stabilities
and estimating kinetic parameters, the majority of works
 Sedaghat & Monajjemzadeh
N N
H H
H 4
O S
SCH3
Phenol-Imine
Fig. 1. Tautomeric forms for H2cdnaphen.
involve transition metal complexes and there are fewer reports
about thermal analysis of organotin complexes. In view of the
industrial application of organotin compounds, we found it
worthwhile to study the thermal behavior of these compounds.
Schiff base in this work (Fig. 1) is asymmetric and
conformationally flexible and contains hard and soft donor
atoms, hence it is worthwhile to synthesize its organotin
complexes and investigate their spectroscopic properties and
thermal behaviors. The results of these studies are reported
here.
EXPERIMENTAL
Materials and Methods
All starting materials were purchased from Merck while
diphenyltin dichloride was supplied by Acros Company and
were all used as received. All solvents were of reagent grade
and used without further purification. Methyl 2-[2-(2-
hydroxynaphthaldimino)ethylamino]-1-cyclopentene-1-dithio-
carboxylate (H2cdnaphen) was prepared from reaction of
Methyl-2-{N-(2-aminoethane)}-amino-1-cyclopentenedithio-
carboxylate (Hcden) [26,27] with 2-hydroxynaphthaldehyde
through literature method [28]. IR spectra were obtained using
an FT BOMEM MB102 spectrophotometer. The 1H and 119Sn
NMR spectra were recorded with a Bruker 400 MHz Avance
Ultrashield spectrometer using TMS and SnMe4 as references,
respectively. Thermogravimetric analyses (TGA) were carried
out using a Perkin-Elmer Diamond thermal analysis method.
The heating rates were controlled at 5 C min-1 under a
nitrogen atmosphere with a 150 ml min-1 flow rate and the
weight loss was measured from ambient temperature up to
1050 C.
478
8 9 10
11
5 6 7
N N
15 14
H 12
O S
3
13
SCH3
2 1
Keto-Amine
Synthesis of SnMe2Cl2(H2cdnaphen)2 (1)
A solution of SnMe2Cl2 (0.032 g, 0.15 mmol) in benzene
(5 ml) was added to a solution of H2cdnaphen (0.111 g, 0.3
mmol) in benzene (11 ml). The mixture was stirred for 3 h at
r.t. During this period, the yellow precipitate was formed. The
product was filtered, washed with benzene and dried over
CaCl2. Yield: 0.097 g (67.3%); m.p.: 165 C (dec.); Anal.
Calcd. for C42H50N4O2S4Cl2Sn: C, 52.5; H, 5.2; N, 5.8%.
Found: C, 52.3; H, 5.2; N, 5.9%. FT-IR (KBr, cm-1):
(NH/OH), 3015-3056, (C=N), 1624, as(Sn-C), 580, s(Sn-
C), 506, (Sn-O), 470. 1H NMR (DMSO-d6): = 1.04 [s,
2 117/119
J( Sn-1H) = 109.1/114.0 Hz, 6H], 1.74 (quint, 3JHH = 7.4
Hz, 4H, H11), 2.40 (s, 6H, SCH3), 2.60 (t, 3JHH = 7.4 Hz, 4H,
H10), 2.78 (t, 3JHH = 7.6 Hz, 4H, H12), 3.77 (m, 4H, H9), 3.87
(m, 4H, H8), 6.78 (d, 3JHH = 9.3 Hz, 2H, H1), 7.21 (t, 3JHH = 7.2
Hz, 2H, H4), 7.39 (t, 3JHH = 8.0 Hz, 2H, H5), 7.65 (d, 3JHH = 7.2
Hz, 2H, H3), 7.75 (d, 3JHH = 9.3 Hz, 2H, H2), 8.00 (d, 3JHH =
8.4 Hz, 2H, H6), 9.06 (d, 3JHH = 8.9 Hz, 2H, H7), 12.22 (t,
3
JHH = 5.8 Hz, 2H, H14), 13.96 (t, 3JHH = 4.3 Hz, 2H, H15),
119
Sn{1H}NMR (DMSO-d6): = -163.3.
Synthesis of [SnPh2Cl2(H2cdnaphen)2].C6H6 (2)
Complex 2 was synthesized as described for compound 1
from SnPh2Cl2 (0.0340 g, 0.10 mmol) and H2cdnaphen (0.074
g, 0.20 mmol) and the yellow product was formed
immediately. Yield: 0.169 g (72.8%); m.p.: 150 C (dec.);
Anal. Calcd. for C58H60N4O2S4Cl2Sn: C, 59.9; H, 5.2; N, 4.8%.
Found: C, 60.1; H, 5.2; N, 4.7%. FT-IR (KBr, cm-1):
(NH/OH), 3041-3062, (C=N), 1640, (Sn-O), 473. 1HNMR
(DMSO-d6): = 1.74 (quint, 3JHH = 7.3 Hz, 4H, H11), 2.40 (s,
6H, SCH3), 2.60 (t, 3JHH = 7.3 Hz, 4H, H10), 2.79 (t, 3JHH = 7.6
Hz, 4H, H12), 3.76 (m, 4H, H9), 3.87 (m, 4H, H8), 6.78 (d,
 Some New Organotin(IV) Schiff Base Adducts
3
JHH = 9.3 Hz, 2H, H1), 7.21 (t, 3JHH = 7.1 Hz, 2H, H4), 7.30
[m, 6H, H3,4,5(SnPh2)], 7.37 (s, 6H, C6H6), 7.39 (m, 2H, H5),
7.65 (d, 3JHH = 7.6 Hz, 2H, H3), 7.76 (d, 3JHH = 9.3 Hz, 2H,
H2), 7.91 [d, 3JHH = 6.9 Hz, 4H, H2,6(SnPh2), 3J(119Sn-1H)
= 112 Hz], 8.00 (d, 3JHH = 8.4 Hz, 2H, H6), 9.07 (d, 3JHH = 8.9
Hz, 2H, H7), 12.22 (t, 3JHH = 5.7 Hz, 2H, H14), 13.98 (m,
3
JHH = 4.2 Hz, 2H, H15), 119Sn{1H}NMR (CDCl3): = -404.0.
Synthesis of SnBu2Cl2(H2cdnaphen)2 (3)
A solution of SnBu2Cl2 (0.037 g, 0.125 mmol) and
H2cdnaphen (0.0926 g, 0.25 mmol) in benzene (15 ml) was
stirred at r.t. for 24 h. Then the solvent was evaporated and
bright green precipitate was collected, washed with benzene
and dried over CaCl2. Yield: 0.066 g (51.0%); m.p.: 140 C
(dec.); Anal. Calcd. for C48H62N4O2S4Cl2Sn: C, 55.1; H, 5.9;
N, 5.3%. Found: C, 54.7; H, 6.0; N, 5.0%. FT-IR (KBr, cm-1):
(NH/OH), 3025-3093, (C=N), 1626, (Sn-O), 469. 1H NMR
(DMSO-d6): = 0.84 [t, 3JHH = 7.3, 6H, H(SnBu2)], 1.30 [m,
4H, H(SnBu2)], 1.53 [m, 4H, H(SnBu2)], 1.62 [m, 4H,
H(SnBu2)], 1.74 (quint, J = 7.4 Hz, 4H, H11), 2.40 (s, 6H,
SCH3), 2.60 (t, 3JHH = 7.3 Hz, 4H, H10), 2.79 (t, 3JHH = 7.6 Hz,
4H, H12), 3.76 (m, 4H, H9), 3.88 (m, 4H, H8), 6.77 (d, 3JHH =
9.3 Hz, 2H, H1), 7.21 (t, 3JHH = 7.1 Hz, 2H, H4), 7.41 (t, 3JHH =
8.3 Hz, 2H, H5), 7.65 (d, 3JHH = 7.1 Hz, 2H, H3), 7.75 (d,
3
JHH = 9.3 Hz, 2H, H2), 8.00 (d, 3JHH = 8.4 Hz, 2H, H6), 9.07
(d, 3JHH = 9.0 Hz, 2H, H7), 12.22 (t, 3JHH = 5.8 Hz, 2H, H14),
13.96 (m, 3JHH = 4.3 Hz, 2H, H15), 119Sn{1H}NMR (DMSO-
d6): = 26.0.
RESULTS AND DISCUSSION
Methyl 2-[2-(2-hydroxynaphthaldimino)ethylamino]-1-
cyclopentene-1-dithiocarboxylate (H2cdnaphen) was prepared
from the reaction of Methyl-2-[N-(2-aminoethane)]-amino-1-
cyclopentenedithiocarboxylate (Hcden) with 2-hydroxy-
naphthaldehyde. The new adducts, were synthesized by the
reaction of SnR2Cl2 (R = Me, Ph, Bu) with the Schiff base in
benzene at room temperature. Stoichiometry of the new
adducts was confirmed by the analytical data and the
integrated 1H NMR spectra were consistent with the empirical
formulae. Compounds 1-3 were obtained only as 1:2 adducts
even when equimolar amounts of the ligand and SnR2Cl2 were
used. The nature of bonding was established by the
spectroscopic investigations.
IR Spectra
In the infrared spectrum of the free ligand no band was
observed in the region 3650-3590 cm-1 attributable to the
stretching vibration of the free OH or NH group indicating
intramolecular hydrogen bond in the ligand. On the other
hand, the bands appearing in the range of 2900-3090 cm-1
were assigned to (O-H) and (N-H) overlapping with the (C-
H). These bands were observed to shift slightly in adducts
relative to free ligands due to the coordination of oxygen atom
with tin and changes in the hydrogen bonding. However, the
position of this band indicates that the ring formed by the
intramolecular hydrogen bond in the ligand is retained in
adducts.
The azomethine C=N band in the IR spectrum of
H2cdnaphen (1628 cm-1) is found at the same position or shift
as in the spectra of adducts only slightly of higher frequency.
This observation indicates that the imine nitrogen is not
involved in coordination with the tin atom. The presence of a
strong band in the spectra of the complexes 1-3 about 1540
cm-1due to the (CO) provides evidence of participation of the
phenolic oxygen in the metal-ligand bonding [21,29]. The
appearance of new bands in the IR spectra of the synthesized
complexes in the region 437-473 cm-1, which may be assigned
to (Sn-O), supports the bonding of oxygen to the tin atom
[23,30,31]. The presence of both s(Sn-C) and as(Sn-C) in the
IR spectrum of the methyl adduct is consistent with the
nonlinear C-Sn-C configuration.
NMR Spectra
H2cdnaphen may exhibit tautomerism between the phenol-
imine and the keto-amine forms (Fig. 1) and has two types of
intramolecular hydrogen bonds (N-HO or NH-O). The
interesting point refarding these types of Schiff bases is the
position of the keto-phenol or amine-imine equilibrium and
the nature of the hydrogen bond in the six-membered chelate
ring in both solid state and solution. In the solid state,
salicylaldimine and naphthaldimine Schiff bases tend to form
the phenol-imine (NH-O) and keto-amine (N-HO),
respectively [32]. However, in solution, both types of
hydrogen bonds may be observed depending on the solvent
[33]. 1H NMR is a powerful technique for the investigation of
479
 Sedaghat & Monajjemzadeh
the position of the keto-phenol or amine-imine equilibrium
and the nature of the hydrogen bonding. In the 1H NMR
spectra of H2cdnaphen in DMSO, the signal CH=N proton
appeared as a doublet and hydroxyl group was broadened.
These observations indicate the proton transfer to imine
nitrogen (NHO) and HCNH coupling. They also indicate
that the keto-amine form of H2cdnaphen is dominating in
DMSO solution.
In the 1H NMR spectra of complexes, the presence of NH
and OH protons indicates that the Schiff base is coordinated
with tin in the neutral form. The obvious splitting of the
phenolic proton peak in the spectrum of complexes relative to
ligand indicates the coordination of oxygen with tin, so more
transfer of O-H proton to imine nitrogen and more coupling
with H-C=N and -CH2 hydrogens occur.
The 1H NMR spectra of 1 show a singlet at 1.03 ppm for
SnMe2 protons accompanied by satellites due to 2J(117/119Sn-
1
H). The 1H NMR spectrum of diphenyltin complex (2) shows
a doublet attributable to the H2,6 of Ph2Sn moiety. This signal
has 119Sn satellites due to 1H-119Sn coupling. No 119Sn
satellites for 3 were observed and the 2J(119Sn-1H) value could
not be extracted from the spectrum because of the complexity
of the methylene multiplets.
The signal attributable to the imine proton (HC=N) in the
spectra of both complexes was not flanked by satellites,
indicating that the N atom was not coordinated with tin(IV).
The lack of a down-field shift in the position of the signal
attributable to SCH3 indicates no participation of the -C=S
group in bonding [34].
The 119Sn{1H}NMR spectra of the complexes show one
sharp singlet significantly at a lower frequency than those of
Table 1. Thermal Decomposition Data for Complexes 1-3
Complex Temp. range DTG peak Weight loss (%)
(C) temp. (C) obs..(calcd.)
1 118-500 220
2 85-145 134
145-350 220
3 148-392 270
480
the original SnMe2Cl2 (+137 ppm), SnPh2Cl2 (-32 ppm) and
SnBu2Cl2 (+123 ppm). 119Sn chemical shift is strongly
dependent on the coordination number of tin atom and an
increase in coordination number produces a large upfield shift.
(119Sn) moves upfield by 60-150 ppm with a change in the
coordination number of tin from 4 to 5 and by 130-200 ppm
from 5 to 6 [35,36]. Therefore, it seems reasonable to assume
that in the adducts 1 and 2 the coordination number of the tin
atom is six in solution. However, the 119Sn signal for 3 lies at
higher frequencies than those for six-coordinate complexes of
butyltin derivatives. This observation suggests that, in
solution, this adduct partially dissociates from and loses the
six-coordination structure.
Thermogravimetric Analyses and Kinetic Studies
The thermogravimetric analyses of the complexes were
carried out through ambient temperature up to 1050 C.
Compounds 1 and 3 are decomposed in one step and 2 in two
steps. The thermal behaviors of the complexes have been
summarized in Table 1.
The thermodynamic activation parameters of
decomposition processes of complexes were evaluated from
TGA curves by using the Coats-Redfern method [37]. The
equation used is in the form:
ln[-ln(1-)/T2] = -E*/RT + ln[AR/E*] (1)
where is the fraction decomposed at a given temperature T
(K) and equals to W/Wf (W is the mass loss up to temperature
T and Wf the mass loss at the completion of the reaction), R is
the gas constant, is the heating rate, A is the frequency factor
Evolved product
71.8 (71.2) C20H22N2S2, C11H8N, C2H4, 2Cl,
2CH3, SCH3
7.5 (6.8) C6H6
48.9 (48.3) C13H12N, 2C6H5, 2Cl, C11H8N
72.9 (72.1) C21H25N2S2, C13H13N2,
2Cl, 2C4H9
 Some New Organotin(IV) Schiff Base Adducts

13.4 15
-ln[-ln(1-)/T2]

-ln[-ln(1-)/T2]
13.2 14
13 a b
13
12.8
12
12.6
12.4 11
12.2 10
1.70 1.80 1.90 2.00 2.10 2.45 2.55 2.65 2.75
-1 -1
1000/T (K ) 1000/T (K )

13 14
-ln[-ln(1-)/T2]

12.8
-ln[-ln(1-)/T2]
c 13.5
12.6 d
13
12.4
12.2 12.5
12
12
1.7 1.8 1.9 2 2.1
1.7 1.8 1.9 2 2.1 2.2
1000/T (K-1) 1000/T (K-1)

Fig. 2. Coats-Redfern plots for the decomposition of complexes (a) 1, (b) 2 (step 1), (c) 2 (step 2) and (d) 3.

and E* is the activation energy. A plot of the left-hand side of
Eq. (1) vs. 1/T gives a straight line (Fig. 2) whose slope and
intercept are used for calculating the values of E* and A,
respectively.
The entropy of activation (S*), the enthalpy of activation
(H*) and the free energy change of activation (G*) were
calculated using the following equations:
S* = Rln(Ah/kBTs)
H* = E* - RT
G* = H* - TS*
where kB is the Boltzman constant, h is the Plank's constant
and Ts is the DTG peak temperature. The various kinetic
parameters calculated are given in Table 2.
The entropy of activation was found to be negative in all
complexes which indicate that the decomposition reactions
proceed with a lower rate than the normal ones and that the
activated complexes have more ordered systems than the
reactants which may be due to the chemisorptions of the
decomposition products [38-42].
CONCLUSIONS
From the spectroscopic studies, it is concluded that in all
(2) complexes, H2cdnaphen acted as a monodentate neutral ligand
and coordinated with the metal as a dangling form through
(3) oxygen atom, while an intramolecular hydrogen bond still
existed between O and N (Fig. 3). Similar proton transfer and
(4) Sn(IV) binding to keto-imine tautomeric form of ligands were
also observed earlier [21,23,43-45].
ACKNOWLEDGMENTS
Support of this work by Shahid Chamran University,
Ahvaz, Iran, is gratefully acknowledged.
481
 Sedaghat & Monajjemzadeh

Table 2. Kinetic Data for the Thermal Decomposition of Complexes 1-3

Complex Step r2 E* (kJ mol-1) H* (kJ mol-1) A (s-1) S* ( J K-1 mol-1) G* (kJ mol-1)
1 1st 0.995 24.61 20.51 0.20 -262.43 149.87
2 1st 0.995 84.22 80.84 3.72108 -83.70 114.90
2nd 0.997 21.81 17.71 0.12 -266.8 149.24
3 1st 0.999 33.98 29.46 2.44 -242.46 161.12

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