Synthesis, characterization, and thermal behavior of 4-chloromethyl-2-(2- hydroxynaphthylidenehydrazino) thiazole and its complexes with Cr(III), Co(II), Ni(II), and Cu(II)

Article abstract of DOI:10.1080/15533170500359430

A new ligand, 4-chloromethyl-2-(2-hydroxynaphthylidenehydrazino) thiazole, has been synthesized from dichloroacetone and 2- hydroxynaphthylidenethiosemicarbazone. Metal complexes of the ligand were prepared from acetate salts of Co(II), Cu(II), Ni(II), and chloride of Cr(III) in dry acetone. Characterization of the ligand and its complexes were made by microanalyses, FT-IR, ¹³C, ¹H NMR, and UV-Visible spectroscopy, magnetic susceptibility, thermogravimetric analysis. In the light of these results it was suggested that two ligands coordinate to each metal atom by hydroxyl oxygen, imino nitrogen and thiazole ring nitrogen to form high spin octahedral complexes with Cr(III), Co(II), Ni(II), and Cu(II). Copyright

Full text of DOI:10.1080/15533170500359430

Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 35:767–771, 2005
Copyright # 2005 Taylor & Francis, Inc.
ISSN: 1553-3174 print/1532-2440 online
DOI: 10.1080/15533170500359430
Synthesis, Characterization, and Thermal Behavior
of 4-Chloromethyl-2-(2-Hydroxynaphthylidenehydrazino)
Thiazole and its Complexes with Cr(III), Co(II), Ni(II),
and Cu(II)
Sinan Saydam and Engin Yilmaz
Department of Chemistry, Faculty of Arts and Science, Firat University, Elazig, Turkey
biochemically relevant studies of metal complexes (Murthy
new ligand, 4-chloromethyl-2-(2-hydroxynaphthylidene- and Reddy, 1981; Streyer, 1995; Razakantoanina and Phung,
A
hydrazino) thiazole, has been synthesized from dichloroacetone
and 2-hydroxynaphthylidenethiosemicarbazone. Metal complexes
of the ligand were prepared from acetate salts of Co(II), Cu(II),
Ni(II), and chloride of Cr(III) in dry acetone. Characterization
of the ligand and its complexes were made by microanalyses,
2000; Royer et al., 1995; Flack et al., 1993; Baumgrass et al.,
2001; Quintana et al., 2000) and found wide range of appli-
cations. Thiazoles represent a very interesting class of com-
pounds because of their wide applications in pharmaceutical,
FT-IR, 13C, 1H NMR, and UV-Visible spectroscopy, magnetic sus- phytosanitary, analytical, and industrial aspects, e.g., as anti-
ceptibility, thermogravimetric analysis. In the light of these results
it was suggested that two ligands coordinate to each metal atom by
hydroxyl oxygen, imino nitrogen and thiazole ring nitrogen to
form high spin octahedral complexes with Cr(III), Co(II), Ni(II),
and Cu(II).
bacterial (Agarwal et al., 1997), fungicide (Sup et al., 1995;
Buristrov and Bobashko, 1964), anti-inflammatory (Hadjipavlou-
Litina and Geronikaki, 1996; Hadjipavlou et al., 1993;
Geronikaki et al., 2003) antihelmintics, antitubercular
(Merchant et al., 1981), anti-HIV (Maass et al., 1993), Antide-
generative (Anna et al., 2003) and hypothermic (Kapoor et al.,
1984) activities and as herbicides (Metzger et al., 1984). In
recent years thiazole based chemisensors have been investi-
gated and showed to be successfuly applicable in biological
systems (Santaun and Mini, 2000; Kim et al., 2000; Torrado
et al., 1998; Thompson et al., 1996).
Keywords 4-chloromethylthiazole, 2-hydroxynaphthylidenehydra-
zine, 4-chlormethyl-2-(2-hydroxynaphthilidenehydrazino)
thiazole, Cr(II), Co(II), Ni(II), Cu(II), complex
It is known that 2-aminothiazole is a biologically active
compound with a broad range of activity and also is an inter-
mediate in the synthesis of antibiotics and dyes. Numerous
thiazole derivative Schiff bases and their transition metal
complexes have been investigated by various techniques
(Sitkowski et al., 1996; Castro et al., 1993; Saydam, 2002;
Hidenori et al., 2001; Elisa et al., 2000; Saydam and Alkan,
2001; James et al., 1997; Mohamed, 2001).
INTRODUCTION
It has long been known that metal ions involve in biological
processes of life and has been the subject of interest. The
modes of action of these metal ions are often complex but
are believed to involve bonding to the hetero atoms of the
heterocyclic residues of biological molecules, i.e., proteins,
enzymes, nucleic acids, etc (Erwin and Omoshile, 1995).
Schiff bases and their metal complexes, played an important
role in the development of coordination chemistry, resulting in
an enormous number of publications, ranging from pure
synthetic work to physicochemical (Luo et al., 2003) and
From these points of view, it is important to study different
types of transition metal complexes of these biologically active
ligands. In this paper, the synthesis and characterizition of the
first row transition metal complexes of the type [ML2] 2H2O
where M is Cr(III), Co(II), Ni(II), and Cu(II) metals, L is a
deprotonated ligand (4-chloromethyl-2-(2-hydroxynaphthyli-
denehydrazino) thiazole), have been studied.
Received 16 August 2005; accepted 9 September 2005.
We would like to thank Firat University for the financial support
(FUBAP 311). I would also like to thank Prof. Dr. Misir Ahmedzade,
and Prof. Dr. Alaaddin C¸ ukurovali for their helpful discussions.
Address correspondence to Sinan Saydam, Department of Chem-
istry, Faculty of Arts and Science, Firat University, Elazig 23169,
Turkey. E-mail: ssaydam@firat.edu.tr
EXPERIMENTAL
Thiosemicarbazide, 2-hydroxynaphthaldehyde, and dichloro-
acetone were purchased from Merck and used without further
767

768
S. SAYDAM AND E. YILMAZ
purification. The ligand synthesized was crystallized from filtered, washed with ethanol, and water; dried at 608C,
ethanol and its purity checked by IR, NMR and elemental yield 10.8 g (87%).
analysis. The elemental analyses were made by using a
LECO-CHNS 932 microanalysis. IR spectrums were taken
using Mattson 1000 FT-IR spectrophotometer as KBr pellets.
1H and 13C NMR spectrums were recorded on Bruker
DpX-400 MHz spectrophotometer. Magnetic susceptibilities
were determined on a Sherwood Scientific magnetic suscepti-
bility balance model MK1 at room temperature using
Hg[Co(SCN)2] as a calibrant. Diamagnetic correction calcu-
lated from Pascal’s constant. Thermogravimetric analyses
The characteristic IR bands (KBr pellets, cm21) are given in
were obtained from a Shimadzu TGA-50 Thermobalance.
Melting points were determined on a Gallenkamp melting
Table 1. The ligand found to be soluble in CHCl3, THF,
point apparatus. Electronic spectrums recorded on a Cecil
methanol, DMSO, DMF, acetone, ethyl acetate and insoluble
CE 5502 Spectrophotometer in the quartz cell path length of
in diethyl ether, n-hexane, and water, slightly soluble in
ethanol. Characteristic 1H NMR peaks are (CCl4 TMS,
1.0 cm. Metal contents of the complexes were determined by
an Ati Unicam atomic absorption spectrophotometer model
d ppm), 8.650 (s, –CH55N), 7.00 (s, 55CH– in thiazole
929, in a solution prepared by decomposing the complexes in
ring). Aromatic protons appeared at about 7.28–8.72 as multi-
concentrated hot HCl þ HNO3 mixture, then evaporating the
plets. C–OH signal at 9.007 ppm, disappeared upon addition of
D2O to the solution, indicating that it is an acidic proton. The
characteristic 13C NMR peaks are: (CCl4 TMS, d ppm), 41.737
solution and subsequent dilution with distilled water to
desired volume.
(C1), 148.987 (C2), 111.822 (C3), 169.875 (C4), 143.640 (C5),
109.408 (C6), 158.300 (C7), 120.059 (C8), 133.738 (C9),
130.547 (C10), 129.419 (C11), 125.203 (C12), 124.607 (C13),
Synthesis of the Ligand (LH)
First, 0.064 mol (5.83 g) of thiosemicarbazide was dis-
129.938 (C14), 1132.870 (C15). Anal. cal. for C15H12ClN3OS
solved in 150 ml of absolute ethanol in 250 ml flask.
(317.80): C 56.69, H 3.81, N 13.22, S 10.09; found: C 56.46, H
0.064 mol (11.02 g) of 2-hydroxynaphthaldehyde dissolved
in 50 ml dry ethanol was added drop-wise to this solution
at room temperature, and then the solution was refluxed
3.74, N 13.54, S 10.66.
General Procedures for the Synthesis of the Complexes
First, 1 mmol of LH dissolved in 20 ml of absolute acetone
then 0.5 mmol of acetate salt of metals dissolved in 10 ml of
for 2 hours, then the temperature brought to room tempera-
ture and stirred for 24 hours. The mixture was poured to
cold water and precipitate was filtered and washed with
water and ethyl alcohol then dried at room temperature,
yield 14.00 g (89%).
.
absolute ethanol (except CrCl3 6H2O) was added drop-wise
and refluxed for 4 hours, then neutralized by dilute NaOH
solution. The precipitated complexes were filtered off washed
with water and ethanol several times and dried at 608C. The
solid compounds were dissolved in 10 ml of tetrahydrofuran
and reprecipitated in 100 ml of diethyl ether then washed
with diethyl ether several times and dried in vacuum at 608C.
The complexes found to be soluble in CHCl3, THF, DMSO,
DMF, methanol, ethyl acetate, slightly soluble in 1,4-
dioxane, dichloro methane, acetone, carbon tetrachloride, and
insoluble in diethyl ether and petroleum ether.
The yield, color, melting point, and characteristic IR bands
as KBr pellets, of the ligand and complexes are given in
Then, 0.04 mol (5.00 g) dichloroacetone was dissolved in Table 1 and Table 2. Anal. cal. for C30H22Cl3CrN6O2S2,
50 ml of dry acetone and added dropwise to 0.04 mol Mol. Wt.: 721.07, C, 49.93; H, 3.05; N, 11.65; S, 8.88, found:
(9.65 g) of 4-chloro-2-(2-hydroxynaphthylidenehydrazino) C 49.72, H 3.30, N 12.06, S 9.23, for C30H22Cl2CoN6O2S2,
thiosemicarbazone dissolved in 150 ml of absolute acetone Mol. Wt.: 692.5, C, 52.03; H, 3.20; N, 12.14; S, 9.26, found:
at 08C in an hour. Then it was stirred at room temperature C 52.22, H 3.18, N 12.58, S 9.04, for C30H22Cl2NiN6O2S2,
for 24 hours followed by 2 hours’ reflux. A green precipi- Mol. Wt.: 692.26, C, 52.05; H, 3.20; N, 12.14; S, 9.26;
tate was filtered off and neutralized by 5% NH3 solution, found: C 52.35, H 3.03, N 12.48, S 9.66; and for
the color of the precipitate turns from light green to C30H22Cl2CuN6O2S2, Mol. Wt.: 697.12, C, 51.69; H, 3.18;
light yellow. After that the precipitate (Figure 2) was N, 12.06; S, 9.20; found: C 52.02, H 3.16, N 12.32, S 9.51.

SYNTHESIS OF A NEW THIAZOLE AND METAL COMPLEXES
769
TABLE 1
Characteristic IR bands of the ligand and its complexes as KBr pellets
Ligand
(LH)
CrL3
CoL2
NiL2
CuL2
n(O–H)
3454 br
1623 m
1567 s
1132 m
1034 w
—
—
—
—
—
n(C55N) azomethine
n(C55N) (thiazole ring)
n(C–O)
n(C–S–C)
n(M–N)
1616 s
1575 s
1097 m
1034 w
621 w
569 w
746 w
1618 m
1579 s
1097 m
1041 w
631 w
525 w
746 w
1616 m
1581 s
1097 m
1041 w
631 w
532 w
746 w
1616 s
1579 s
1097 m
1034 w
633 w
569 w
746 w
n(M–O)
n(C–Cl)
—
743 w
Key: s (strong), m (medium), br (broad), w (weak).
RESULTS AND DISCUSSION
coordination of ligand to metal atom over nitrogen of azomethine
(Nakamura et al., 1979) and oxygen of hydroxyl groups. A broad
band at 3400cm21 was observed in the spectra of the Cr(III)
complex due to the presence of water molecule in the complex.
The shifts of n(C–O) band at 1132cm21 to lower energy
suggests that the weakening of n(C–O) and formation of
stronger bond between M–O. The shifts of the n(C55N) vibration
of the thiazole group in all the complexes to lower energy suggest
that nitrogen atom of the ring also contrubutes to the complexa-
tion. Practically unchanged n(C–S–C) vibration at 1034cm21
of the thiazole ring (Castro et al., 1993) indicates that the
thiazole group does not coordinate to metal from the sulfur
atom. A weak band around 631 cm21 in the complexes is
absent in the ligand spectrum assigned to n(M–O) vibration.
Another weak band appeared in the spectra of the complexes at
525, 532, and 569 cm21attributed to n(M–N) vibration
(Williams and Fleming, 1989). From these observations it was
suggested that, the azomethine nitrogen, the nitrogen atom in
thiazole ring and hydroxy oxygen involve in the complexation
reaction as donor atoms.
The synthesis of ligands (Figures 1 and 2) was performed in
two steps. In the first step 4-chloro-2-(2-hydroxynaphthylide-
nehydrazino) thiosemicarbazone was obtained. In the second
step the ligand molecule was formed by the ring closure
reaction of 1,3-dichloroacetone and 4-chloro-2-(2-hydroxy-
naphthylidenehydrazino) thiosemicarbazone. Authentication
of the ligand was checked by FT-IR, 1H and 13C NMR,
elemental analysis. Then the coordination compounds were
synthesized in dry acetone.
IR Spectra
Table 1 lists the major bands of the ligand and its com-
plexes. In the IR spectra of the ligand (LH) the most character-
istic bands appeared at 3454 cm21 n(O–H), 1567 cm21
n (C55N thiazole ring), 1623 cm21 n(C55N azomethine), and
1132 cm21 n(C–O), 1034 cm21 n(C–S–C) (Castro et al.,
1993) and 748 cm21 n(C–Cl).
The azomethine vibration of the ligand at 1623 cm21 was
shifted to lower frequency after complexation, which is 1616,
1618, 1616, and 1616cm21 for Cr(III), Co(II), Ni(II), and
Cu(II) complexes respectively. At the same time n(C–O) band
at 1132cm21 in the free ligand is shifted to lower frequency
UV-Vis. Spectra and Magnetic Moments
The electronic spectrum of the Schiff base LH and its com-
after complexation, which means that these shifts are due to plexes were recorded in THF. Two very strong bands at 345 nm
TABLE 2
Formulas, formula weights, colors, melting points, yields, metal contents of the ligand and its complexes with
transition metals of Cr(III), Co(II), Ni(II), and Cu(II)
FW
g/mole
Magnetic
susceptibility BM
Mp
(8C)
Yield
%
Compounds
Color
LH, C15H12ClN3O2S
317.80
721.07
692.26
692.50
697.12
—
Light green
Dark brown
Light brown
Light green
Dark green
201
195
205
215
150
87
70
70
72
58
CrL2Cl, C30H22Cl3N6O4S2Cr
CoL2, C30H22Cl2N6O4S2Co
NiL2, C30H22Cl2N6O4S2Ni
CuL2, C30H22Cl2N6O4S2Cu
4.81
2.87
2.94
1.48

770
S. SAYDAM AND E. YILMAZ
Cu(II) complexes display a wide range of geometries, often
with a low symmetry and in most geometries the electronic
spectra exhibits a very broad band with maximum which
contains all the expected transitions (Greenwood and
Earnshaw, 1984). The UV-visible spectra of the Cu(II)
2
complex, has a strong band at 450 nm, assigned to 2Eg ! T2g
transition with a tailing to higher wavelength which is well
known for octahedral copper complexes, (Elsonbatı et al.,
1992; Mojumdar et al., 1999). The magnetic moment of 1.5
BM indicates some sort of molecular association that could be
achieved through bridged ligand (Omar and Mohamed, 2005)
or caused by spin orbit coupling.
FIG. 1. 4-Chloromethyl-2-(2-hydroxynaphthylidenehydrazino)
thiazole (LH).
The thermogram of the ligand shows that the weight loss
begins at 2308C and decomposes at three steps, which are
230–2608C, 260–4008C and 400–7508C leaving 12%
residue. The first step which has 6% weight lost corresponds
to (–OH) group (calculted 5.4%). The second and third steps
of the decomposition take place between 230–2608C corre-
sponding to loss of 2-chloromethylthiazole group and the
third step takes place between 400–7508C with the complete
decomposition of the ligand.
and 240 nm were observed in the spectra of the ligand, which
are attributed to n ! pꢀ and p ! pꢀ transitions in the
aromatic ring and C55N chromophore (Drago, 1992).
Chrome complexes have two absorption bands, 600, 400 and
4
4
(as a shoulder) nm and assigned to A2g ! T2g(F), and
4
4A2g ! T1g(F). The 10 Dq energy of the Cr(III) complex cal-
culated from the Tanebe–Sugano diagrams was found to be
16670 cm21 with a Racah parameter of 925 cm21. The
observed magnetic moment value of 4.20 BM and the elec-
tronic spectra of the complex support the octahedral structure
for the complex. The cobalt complex have two bands one at
740 nm and the other at 420 nm, which are assigned to
All the complexes have similar decomposition pattern in
two steps. In the first step 40% of weight loss between 225–
3808C corresponds to the loss of 2-chloromethylthiazole
(C4H3ClNS) group (calculated ꢁ38.5% for the all complexes).
The complexes further decompose to yield 13.5%, 12.8%,
13.2%, and 12.3%, residue corresponding to Cr2O3 (calculated
10.9%), CoO (calculated 11.0%), NiO (calculated 10.9%), and
CuO (calculated 11.3%), respectively.
4
4
4
4T1g ! T2g(F), T1g ! T1g(P) transitions respectively. Cal-
culated 10 Dq energy of the Co(II) complex is 1480 cm21
and the Racah parameter is 600 cm21. From the position of
the bands and the magnetic moment value of 4.8 BM the
geometry of the cobalt complex is presumably octahedral.
d-d transitions of the nickel complex at 625 nm and 420, corre-
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