Synthesis and characterization of new Schiff bases and their cobalt(II), nickel(II), Copper(II), Zinc(II), cadmium(II) and mercury (II) complexes

Article abstract of DOI:10.1081/SIM-200059233

Nickel(II), copper(II), cobalt(II), zinc(II), cadmium(II) and mercury(II) complexes chelates containing the Schiff base ligands methyliminoisonitroso-2- acetylnaphthalene (HL¹) and benzyliminoisonitroso-2-acetylnaphthalene (HL²) have been prepared. The results suggest that the Schiff bases function as bidentate ligands and indicate a mononuclear structure for the Cu(II) complexes with square-planar geometry. The Ni(II), Zn(II), Hg(II) and Cd(II) complexes are of tetrahedral geometry and the Co(II) complexes with octahedral geometry with water molecules at the axial positions. These compounds have been characterized by elemental analyses, magnetic susceptibility, mass, IR, UV, ¹H and ¹³C NMR spectroscopy. Copyright

Full text of DOI:10.1081/SIM-200059233

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Synthesis and Characterization of New Schiff Bases
and Their Cobalt(II), Nickel(II), Copper(II), Zinc(II),
Cadmium(II) and Mercury(II) Complexes
Selma Y. Uçan a , Mustafa Uçan a & Bedrettin Mercimek b
a Department of Chemistry, Faculty of Arts and Sciences , Niğde University , Niğde, Turkey
b Department of Chemistry, Faculty of Education , Selçuk University , Konya, Turkey
Published online: 15 Feb 2007.
To cite this article: Selma Y. Uçan , Mustafa Uçan & Bedrettin Mercimek (2005) Synthesis and Characterization of New Schiff
Bases and Their Cobalt(II), Nickel(II), Copper(II), Zinc(II), Cadmium(II) and Mercury(II) Complexes, Synthesis and Reactivity in
Inorganic, Metal-Organic, and Nano-Metal Chemistry, 35:5, 417-421
To link to this article: http://dx.doi.org/10.1081/SIM-200059233
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Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 35:417–421, 2005
Copyright # 2005 Taylor & Francis, Inc.
ISSN: 0094-5714 print/1532-2440 online
DOI: 10.1081/SIM-200059233
Synthesis and Characterization of New Schiff Bases and Their
Cobalt(II), Nickel(II), Copper(II), Zinc(II), Cadmium(II) and
Mercury(II) Complexes
Selma Y. Uc¸an and Mustafa Uc¸an
Department of Chemistry, Faculty of Arts and Sciences, Nigde University, Nigde, Turkey
˘
˘
Bedrettin Mercimek
Department of Chemistry, Faculty of Education, Selc¸uk University, Konya, Turkey
metal ions have also provoked wide interest because they
Nickel(II), copper(II), cobalt(II), zinc(II), cadmium(II) and possess a diverse spectrum of biological and pharmaceutical
mercury(II) complexes chelates containing the Schiff base
ligands methyliminoisonitroso-2- acetylnaphthalene (HL1) and
activities, such as antitumor and antioxidative activities, as
well as the inhibition of lipid peroxidation, etc (Uc¸an et al.,
benzyliminoisonitroso-2-acetylnaphthalene (HL2) have been
prepared. The results suggest that the Schiff bases function as
1998; Yang et al., 2000; Yıldırım et al., 2003).
The present investigation is concerned with the preparation
bidentate ligands and indicate a mononuclear structure for the
Cu(II) complexes with square-planar geometry. The Ni(II), and characterization of Ni(II), Cu(II), Co(II), Zn(II), Cd(II) and
Zn(II), Hg(II) and Cd(II) complexes are of tetrahedral geometry
and the Co(II) complexes with octahedral geometry with water
Hg(II) chelates with the bidentate Schiff bases derived from
amines with isonitroso-2-acetylnaphthalene (Figure 1).
molecules at the axial positions. These compounds have been
characterized by elemental analyses, magnetic susceptibility,
1
mass, IR, UV, H and 13C NMR spectroscopy.
EXPERIMENTAL
Materials and Measurements
Keywords Schiff base ligands, spectra, transition metal complexes
Isonitroso-2-acetylnaphthalene was prepared according to
published procedures (Tu¨mer et al., 1997; Tuna et al., 2003).
The amine compounds (methylamine and benzylamine) were
obtained from Fluka and were used without further purifi-
cation. All solvents were obtained from E. Merck or Fluka.
The metal salts were purchased from E. Merck and were
used as received. Elemental analyses (C, H, N) were performed
using a Carlo-Erba 1106 elemental analyzer. UV-Vis. spectra
were recorded on a Shimadzu UV-160A spectrophotometer.
The samples were dissolved in DMF and the spectra were
recorded in the 800–200 nm range. The magnetic moments
of the complexes were measured by the Gouy method on a
INTRODUCTION
The formation of Schiff bases by the condensation of amines
with aldehydes or ketones is well known (Amirnasr et al., 2002;
˙
Deveci and Irez, 1995; Dreos et al., 2003; Garg and Kumar,
¨
2003; Karatas¸ and Uc¸an, 1998; Koksal et al., 1996; Mercimek
et al., 1999; Mokles and Elzaher, 2001). Ligands derived by
condensation of a primary amine and an active carbonyl
group contain the azomethine group and form stable complexes
with metal ions, especially if the amine and the carbonyl
compound contain a second functional group sufficiently near
the site of condensation to form a five- or six-membered
chelate ring upon chelation (Park et al., 1998; Ray et al.,
2003; Tarafder et al., 2002; Tu¨mer et al., 1997; Tuna et al.,
2003). In addition, a great many Schiff base complexes with
1
type D-104 Newport Instrument. H and 13C NMR spectra
were recorded on a Varian XL 200 spectrometer with the
samples dissolved in DMSO-d6 using TMS as internal
standard. The IR spectra were recorded in KBr pellets in the
range 4000–400 cm21 on a Pye-Unicam SP 1025 model
FT-IR spectrometer.
Synthesis of Schiff Base Ligand
Received 27 March 2004; accepted 19 February 2005.
Address correspondence to S. Y. Uc¸an, Department of Chemistry,
Methyliminoisonitroso-2-acetylnaphthalene [HL1] was
prepared by a condensation method. Methylamine (0.18 g,
6 mmol) was dissolved in MeOH (10 mL) and was added to a
˘
Faculty of Arts and Sciences, Nigde University, Nigde 51200, Turkey.
E-mail: selmaucan@nigde.edu.tr
˘
417

418
S. Y. UC¸ AN ET AL.
dried in a vacuum desiccator over CaCl2. Benzyliminoisoni-
troso-2-acetylnaphthalene was prepared in a similar fashion.
Synthesis of Complexes
The complexes were synthesized by a modification of litera-
˙
ture preparations (Deveci and Irez, 1995; Mokles and Elzaher,
2001; Tarafder et al., 2002; Tu¨mer et al., 1997). A solution of
.
.
Ni(AcO)2 4H2O (0.124 g, 0.5 mmol), Cu(AcO)2 H2O
.
(0.099 g, 0.5 mmol), Co(AcO)2 4H2O (0.124 g, 0.5 mmol),
.
.
Zn(AcO)2 2H2O (0.109 g, 0.5 mmol), Cd(AcO)2 2H2O
(0.133 g, 0.5 mmol) or Hg(AcO)2 (0.159 g, 0.5 mmol), in
EtOH (10 mL) was added to a solution of HL1 (0.212 g,
1 mmol) in EtOH. The mixture was refluxed for 3 h at 70 8C.
The precipitated complex was filtered, washed with cold
EtOH and dried in a vacuum desiccator over CaCl2. The same
experimental procedure was followed in the preparation
of Ni(II), Cu(II), Co(II), Zn(II), Cd(II) and Hg(II) Complexes
of [HL2].
FIG. 1. Structures of the ligands.
solution of isonitroso-2-acetylnaphthalene (1.19 g, 6 mmol) in
20 mL of MeOH. The reaction mixture was stirred for 2 h
and then left overnight at room temperature. The solid reaction
product was filtered and washed with cold ethanol. The ligand
was recrystallized from dichloromethane/ethanol (1:1) and
TABLE 1
Physical properties and elemental analysis of the ligands and complexes
Analysis found (calcd.) %
Yield
(%)
M.p.
(8C)
meff
(B.M.)
Compound
FW.
212
Color
Yellow
C
H
N
HL1 (C13H12N2O)
90
92
81
83
95
79
80
86
82
76
80
92
89
86
84
251
283
220
137
196
126
79
73.56
(73.39)
64.9
5.69
(5.77)
4.6
13.19
(13.35)
11.64
(11.79)
11.52
(11.26)
10.82
(10.5)
11.48
(11.22)
10.47
(10.35)
8.99
[Ni(L1)2] C26H22NiN4O2
[Cu(L1)2] C26H22CuN4O2
[Co(L1)2(H2O)2] C26H26CoN4O4
[Zn(L1)2] C26H22ZnN4O2
[Cd(L1)2] C26H22CdN4O2
[Hg(L1)2] C26H22HgN4O2
HL2 C19H16N2O
481
486
517
487
534
623
288
633
638
669
640
687
775
Green
3.5
(64.74)
64.25
(4.43)
4.56
Brown
1.66
(64.15)
60.35
(4.46)
5.06
Red
4.7
(60.28)
64.01
(4.92)
4.54
Light yellow
Yellow
Orange
Yellow
Green
Diamag.
Diamag.
Diamag.
(63.91)
58.38
(4.48)
4.14
(58.3)
50.12
(4.04)
3.55
(49.97)
79.14
(3.32)
5.29
(8.87)
9.71
(9.6)
(78.99)
72.06
(5.23)
4.77
[Ni(L2)2] C38H30NiN4O2
[Cu(L2)2] C38H30CuN4O2
[Co(L2)2(H2O)2] C38H34CoN4O4
[Zn(L2)2] C38H30ZnN4O2
Cd(L2)2 C38H30CdN4O2
[Hg(L2)2] C38H30HgN4O2
284
197
184
141
163
139
4.0
8.84
(8.78)
8.77
(71.88)
71.51
(4.61)
4.73
Brown green
Red
1.75
(71.38)
68.15
(4.68)
5.11
(8.67)
8.36
5.7
(67.97)
71.34
(5.03)
4.72
(8.24)
8.75
Light yellow
Yellow
Orange
Diamag.
Diamag.
Diamag.
(71.26)
66.42
(4.64)
4.4
(8.68)
8.15
(66.39)
58.87
(58.7)
(4.26)
3.9
(3.75)
(8.09)
7.22
(7.14)

TABLE 2
Characteristic IR bandsa of the ligands and their complexes (KBr, cm21
)
Electronic
data in DMSO
IR spectra (cm21
)
Molecular ion
found (calc.)a
212.1 (212)
Compounds
n(O–H)
N(C–H)a
n(C–H)
n(C55N)
n(N–O)
N(M–N)
N(M–O)
l
max(cm21
)
HL1
3230 b
3100 w
3055 w
3050 w
3070 w
3050 w
3060 w
3045 w
3050 w
3055 w
3050 w
3075 w
3085 w
3070 w
3046 w
2770 w
2820 w
2800 w
2750 w
2700 w
2930 w
2900 w
2700 w
2850 w
2820 w
2880 w
2860 w
2830 w
2825 w
1645–1625 s
1614–1569 s
1622–1599 s
1629–1605 s
1613–1576 s
1617–1579 s
1621–1585 s
1645–1621 s
1605–1585 s
1600–1580 s
1621–1600 s
1620–1576 s
1622–1585 s
1614–1585 s
990 w
925 w
924 w
920 w
913 m
924 w
925 m
990 w
925 w
930 w
925 w
916 w
940 m
916 m
[Ni(L1)2]
[Cu(L1)2]
[Co(L1)2(H2O)2]
[Zn(L1)2]
[Cd(L1)2]
[Hg(L1)2]
HL2
535 w
540 w
481 w
580 w
485 w
489 w
482 w
475 w
436 w
481 w
431 w
437 w
15.625
15.350
16.452
29.186
3420 b
517.1 (517)
3208 b
3415 b
288.1(288)
633.3 (633)
[Ni(L2)2]
[Cu(L2)2]
[Co(L2)2(H2O)2]
[Zn(L2)2]
Cd(L2)2
490 w
500 w
484 w
481 w
530 w
481 w
430 w
400 w
431 w
420 w
425 w
420 w
[Hg(L2)2]
ab: broad, s: strong, m: medium, w: weak.

420
S. Y. UC¸ AN ET AL.
TABLE 3
NMR spectral data (in ppm) of the ligands and their complexes
1H NMR signals
Aromatic
proton
13C NMR signals
Compounds
C55NOH
CH55N
CH3
CH2
C55NO
CH55N
CH3
CH2
HL1
8.90
8.52
8.46
8.14
8.08
2.48
2.38
8.38–7.80
8.15–7.36
8.02–7.18
7.96–7.06
189,59
186.70
188.57
185.12
148,58
147.25
147.54
142.34
28.30
20.12
[Ni(L1)2)
HL2
8.62
3.85
3.16
44.43
40.00
[Ni(L2)2)
RESULTS AND DISCUSSION
135.88–125.75 ppm range are assigned to the carbon atoms
of the aromatic rings. The signals observed at 28.30 and
44.43 ppm may be attributed to the carbon atoms of the CH3
The reaction of isonitroso-2-acetylnaphthalene with methyl-
amine or benzylamine in MeOH gave the desired substituted
methyliminoisonitroso-2-acetylnaphthalene (HL1) and benzy-
liminoisonitroso-2-acetylnaphthalene (HL2) in a single step
(Figure 1). The ligands are soluble in EtOH, MeOH, chloro-
methane and diethyl ether. The addition of Ni(II), Cu(II),
Co(II), Zn(II), Hg(II) or Cd(II) acetate dissolved in methanol
to an alcoholic solution of the ligands gave colored complexes.
All of the complexes are soluble in DMSO, THF and DMF, but
insoluble in the other common organic solvents. The compo-
sitions of the Schiff bases and their complexes have been
verified by elemental analyses (Table 1).
¨
and CH2 groups, respectively (Koksal et al., 1996; Tarafder
et al., 2002; Zishen et al., 1990).
The mass spectra of the ligand HL1 gave molecular ion at
m/z 212 and it’s the Co(II) complex at m/z 517. Molecular
ion of HL2 appeared at m/z 288 and its Ni(II) complex
showed peak at m/z 633.
The electronic spectra of all the complexes were recorded in
1023 M DMF solution at room temperature. The free Schiff
base exhibits two absorption bands in the 252–275 and
305–324 nm regions. These bands are attributed to p ! pꢀ
transitions, the first being due to the aromatic ring and the sec-
ond the imino group. In the complexes, the imino p ! pꢀ tran-
sition is shifted to a longer wave length as a consequence of
coordination to the metal, confirming the formation of Schiff
base metal complexes.
In the IR spectral data of the ligands, bands at 3230–3208,
3100–3050 cm21
,
1645–1621 cm21 and 990–980 cm21
belong to O–H, C–H(arom), C55N and N–O stretching bands,
respectively. Evidence of nitrogen bonding of the azomethine
C55N group to the metal ion stems from the shift of the
n(C55N) frequency to lower frequencies by 16–41 cm21 in
The electronic spectra of the Cu(II) complex shows an
2
2
absorption band at 15.350 cm21 attributed to the Bıg ! Aıg
transition, which is compatible with this complex having a
square-planar structure. The electronic spectra of the Ni(II)
complexes exhibit two bands at 15.625 cm21 and
˙
all of the complexes (Amirnasr et al., 2002; Deveci and Irez,
1995; Dreos et al., 2003; Garg and Kumar, 2003; Mokles and
Elzaher, 2001; Tarafder et al., 2002; Tu¨mer et al., 1997).
New bands in the complexes at 580–420 cm21 are attributed
to the n(M–N) and n(M–O) vibrations, respectively (Mokles
and Elzaher, 2001; Tarafder et al., 2002; Uc¸an et al., 1998;
Zishen et al., 1990).
The 1H NMR spectra of the ligands exhibited a singlet peak
for the OH protons of the oxime groups at 8.90–8.62 ppm. For
the N55CH protons, a singlet occurs in the 8.52–8.14 ppm
region (Karatas¸ and Uc¸an, 1998; Mercimek et al., 1999;
Tu¨mer et al., 1997; Tuna et al., 2003). The broad multiplet at
8.38–7.18 ppm, has been assigned to the aromatic ring protons.
A singlet observed at 2.48 ppm corresponds to the methyl
3
3
34.483 cm21. The former is probably due to the Tı ! Tı(P)
transition and the latter due to the charge transfer transition
3
3
of tetrahedral geometry. The lowest energy band, Tı ! T2,
is not observed in the spectrum. The Co(II) complex show
two bands at 16.452 cm21 and 18.530 cm21 corresponding to
4
4
the transitions 4Tı(F) ! A2(F) and 4Tı(F) ! Tı(P), respecti-
vely. All these findings favor an octahedral geometry for this
complex. The spectrum of the Zn(II) complex shows an
absorption band at 29.186 cm21 attributed to the L ! M
(charge transfer) transition, which is compatible with this
complex having a tetrahedral structure.
protons. The methylene protons at 3.85 ppm (Deveci and
˙
The magnetic moment data of the complexes are given in
Table 1. The values 1.66 and 1.75 B.M. observed for
[Cu(L1)2] and [Cu(L2)2], respectively, reveal the square-
planar nature around the Cu(II) ion (Karatas¸ and Uc¸an, 1998;
¨
Irez, 1995; Koksal et al., 1996; Mercimek et al., 1999; Tuna
et al., 2003).
In the 13C NMR spectra of the ligands, the signals at
189.59–188.57 and 148.58–147.54 ppm are attributed to the
carbon atoms of the oxime groups and the carbon atoms of
the azomethine groups, respectively (Park et al., 1998; Ray
et al., 2003; Tarafder et al., 2002). All the signals in the
¨
Koksal et al., 1996; Mercimek et al., 1999). The values of
nickel complexes [Ni(L1)2] and [Ni(L2)2] are 3.5 and 4.0
¨
B.M., respectively (Koksal et al., 1996; Mercimek et al.,

SYNTHESIS AND CHARACTERIZATION OF NEW SCHIFF BASES
421
¨
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