Synthesis and Characterization of Cu(II), Co(II), Ni(II), and Zn(II) Complexes of a Schiff Base Derived from 1-Amino-5-benzoyl-4-phenyl-1H- pyrimidine-2-one and 3-Hydroxysalicylaldehyde

Article abstract of DOI:10.1081/SIM-120026545

Cu(II), Co(II), Ni(II) and Zn(II) metal complexes of a new heterocylic Schiff base derived from 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-one with 3-hydroxy-salicylaldehyde have been synthesized and characterized on the basis of elemental analyses, electronic, IR and ¹H NMR spectra, molar conductivity measurements, magnetic moment measurements and thermogravimetric analyses (TGA). It has been found that the Schiff base behaves as a neutral bidentate (NO) or tridentate (ONO) ligand forming chelates with 1:2 (metal:ligand) stoichiometry and octahedral geometry. The conductivity data for the Ni(II) complex is consistent with that expected for a weak electrolyte.

Full text of DOI:10.1081/SIM-120026545

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Synthesis and Characterization of Cu(II), Co(II), Ni(II),
and Zn(II) Complexes of a Schiff Base Derived from
1‐Amino‐5‐benzoyl‐4‐phenyl‐1H‐pyrimidine‐2‐one and
3‐Hydroxysalicylaldehyde
Mehmet Sönmez a , Abdulkadir Levent a & Memet Şekerci b
a Department of Chemistry, Faculty of Science and Arts, Yüzüncü Yıl, Universty, Van, 65080,
Turkey
b Department of Chemistry, Faculty of Science and Arts, Firat University, Elazığ, 23169,
Turkey
Published online: 15 Feb 2007.
To cite this article: Mehmet Snmez , Abdulkadir Levent & Memet ekerci (2003) Synthesis and Characterization of Cu(II),
Co(II), Ni(II), and Zn(II) Complexes of a Schiff Base Derived from 1‐Amino‐5‐benzoyl‐4‐phenyl‐1H‐pyrimidine‐2‐one and
3‐Hydroxysalicylaldehyde, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 33:10, 1747-1761, DOI: 10.1081/
SIM-120026545
To link to this article: http://dx.doi.org/10.1081/SIM-120026545
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SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY
Vol. 33, No. 10, pp. 1747–1761, 2003
Synthesis and Characterization of Cu(II), Co(II),
Ni(II), and Zn(II) Complexes of a Schiff Base
Derived from 1-Amino-5-benzoyl-4-phenyl-1H-
pyrimidine-2-one and 3-Hydroxysalicylaldehyde
1
2
Mehmet So¨nmez,1, Abdulkadir Levent, and Memet ꢀSekerci
*
1Department of Chemistry, Faculty of Science and Arts, Yu¨zu¨ncu¨ Yıl,
Universty, Van, Turkey
2Department of Chemistry, Faculty of Science and Arts, Fırat University,
Elazıg˘, Turkey
ABSTRACT
Cu(II), Co(II), Ni(II) and Zn(II) metal complexes of a new heterocylic
Schiff base derived from 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-
one with 3-hydroxy-salicylaldehyde have been synthesized and charac-
1
terized on the basis of elemental analyses, electronic, IR and H NMR
spectra, molar conductivity measurements, magnetic moment measure-
ments and thermogravimetric analyses (TGA). It has been found that the
Schiff base behaves as a neutral bidentate (NO) or tridentate (ONO)
ligand forming chelates with 1:2 (metal:ligand) stoichiometry and
*
Correspondence: Mehmet So¨nmez, Department of Chemistry, Faculty of Science
and Arts, Yu¨zu¨ncu¨ Yıl, Universty, 65080 Van, Turkey; E-mail: vansonmez@
hotmail.com.
1747
DOI: 10.1081/SIM-120026545
0094-5714 (Print); 1532-2440 (Online)
www.dekker.com
Copyright D 2003 by Marcel Dekker, Inc.

1748
So¨nmez, Levent, and ꢀSekerci
octahedral geometry. The conductivity data for the Ni(II) complex is
consistent with that expected for a weak electrolyte.
Key Words: N-Aminopyrimidine; 3-Hydroxysalicylaldehyde; Metal
complexes.
INTRODUCTION
Metal complexes of Schiff bases have been described in a huge number
of publications ranging from the purely synthetic to modern physico-
chemically to biochemically relevant studies of these complexes. Schiff
bases are compounds containing the azomethine group (RC=N-) and are
usually formed by the condensation of a primary amine with an active
carbonyl compound. Bidentate or tridentate Schiff bases derived from
substituted salicylaldehyde derivatives and their transition metal complexes
have been studied for many years.[1–5] In recent years, metal complexes of
Schiff bases have attracted considerable attention due to their remarkable
antifungal, antibacterial and antitumor activity.[6,7] Schiff base complexes
derived from 4-hydroxysalicylaldehyde and amines have strong anticancer
activity.[8] Transition metal cation compounds with pyrimidine derivatives
of nucleic acids (such as uracyl, cytosine and thymine) were also of special
interest.[9]
The present paper reports the synthesis of a new Schiff base ligand
(Figure 1) containing a pyrimidine ring and its metal complexes. Spectral
and magnetic studies have been used to characterize the structure of each of
1
the complexes. H NMR spectra were obtained to determine the structure of
the ligand LH2.
Figure 1. Structure of the ligand LH2.

Complexes of a Schiff Base
1749
EXPERIMENTAL
Materials and Methods
MeOH, EtOH, CHCl3, DMF, toluene, diethyl ether, n-heptane and 3-
hydroxy-salicylaldehyde were obtained from Fluka or Aldrich. The metal
salts Cu(OOCCH3)2ꢀH2O, Co(OOCCH3)2ꢀ4H2O, Zn(OOCCH3)2ꢀ2H2O and
NiCl2ꢀ6H2O were obtained from E. Merck. All solvents were dried and
purified before use. 1-Amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-one was
prepared as described previously.[10]
Elemental analyses (C, H, N) were performed using a Carlo Erba 1106
elemental analyser. IR spectra were obtained using KBr discs (4000–400)
cm–1 on a Bio-Rad-Win-IR spectrophotometer. Electronic spectra in the
200–900 nm range were obtained in DMF on a Unicam UV2-100 UV/
Visible spectrophotometer. Magnetic measurements were carried out by the
Gouy method using Hg[Co(SCN)4] as calibrant. Molar conductances of the
Schiff base ligand and their transition metal complexes were determined in
DMF at room temperature using a Jenway model 4070 conductivity meter.
1
The H NMR spectrum of the Schiff base was recorded with a Varian XL-
200 NMR instrument. TGA measurements were carried out using a Shi-
madzu-50 thermal analyzer.
Preparation of the Schiff Base (LH2)
The Schiff base ligand was prepared by the condensation of the 1-
amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-one (0.291 g, 1.00 mmole)
with 3-hydroxysalicylaldehyde (0.138 g, 1.00 mmole) in ethanol (40 mL)
by boiling the mixture under reflux for 2 h. The precipitated ligand was
filtered, recrystallized from EtOH and dried in a vacuum desiccator.
Preparation of the Schiff Base Complexes
The ligand (0.82 g, 2.0 mmole) was dissolved in 30 mL of chloroform,
and a solution of 1.0 mmole of the metal salt [Cu(OOCCH3)2ꢀH2O (0.20 g),
Co(OOCCH3)2ꢀ4H2O (0.25 g), Zn(OOCCH3)2ꢀ2H2O (0.22 g) and NiCl2ꢀ
6H2O (0.24 g)] in 15 mL methanol was added dropwise with continuous
stirring. The mixture was stirred further for 1.5–2.5 h. at 80 °C. The pre-
cipitated solid was then filtered off, washed with diethyl ether, followed by
cold ethanol and dried in a vacuum desiccator.

1750
So¨nmez, Levent, and ꢀSekerci

Complexes of a Schiff Base
1751
Figure 2. Synthesis scheme for the preparation of the ligand LH2.
RESULTS AND DISCUSSION
The newly synthesized Schiff base ligand and its complexes are very
stable at room temperature in the solid state. The ligand is soluble in
common organic solvents. However, its metal complexes are generally
soluble in DMF and DMSO. The colors, yields, melting points, elemental
analyses and molar conductances of all the compounds are presented in
Table 1. The analytical data are in good agreement with the proposed
stoichiometry of the complexes. Condensation of 3-hydroxysalicylaldehyde
with 1-amino-5-benzyl-4-phenyl-1H-pyrimidine-2-one readily gives the
1
corresponding imine, which is easily identified by its IR, H NMR spectra
(Figure 2).
Tridentate and bidentate complexes were obtained from reaction of a
1:2 molar ratio of metal ions and LH2 ligand. The ligand LH2, on reaction
with Co(OOCCH3)2ꢀ4H2O, Cu(OOCCH3)2ꢀH2O, Zn(OOCCH3)2ꢀ2H2O, and
NiCl2ꢀ6H2O yields complexes corresponding to the general formulas
[Co(LH)2]ꢀH2O, [Cu(LH)2]ꢀ2H2O, [Zn(LH)2]ꢀH2O, and [Ni(LH2)2Cl2]ꢀ2H2O
respectively. The analytical data for all of the complexes are presented in
Tables 1 and 2. The complexes were prepared by the general reaction
shown below.
methanol=chloroform
2LH2 þ MðOOCCH3Þ2ꢀnH2O þ yH2O
ꢀmH2O þ 2CH3COOH þ xH2O
M ¼ CoðIIÞ CuðIIÞ ZnðIIÞ
½MðLHÞ2Š
n ¼
m ¼
x ¼
y ¼
4
1
1
2
2
1
4
ꢁ
1
ꢁ
1
ꢁ
methanol=chloroform
2LH2 þ NiCl2ꢀ6H2O
½NiðLH2Þ2Cl2Šꢀ2H2Oþ4H2O

1752
So¨nmez, Levent, and ꢀSekerci

Complexes of a Schiff Base
Infrared Spectral Study
1753
Table 2 presents the most important IR spectral bands of the ligand
LH2 in all the metal complexes. The IR spectra of the Schiff base ligand
LH2, showed a broad band at 3616 cm–1 which may be due to n(OH). The
free n(OH) is generally observed[11–13] between 3500–3650 cm–1. The
observed low frequency of this band is due to intramolecular hydrogen
bonding between H of OH and the azomethine nitrogen suggesting the
presence of structure b (see Figure 1) at least in the solid state.
The intense band at 1273 cm–1 present in the IR spectrum of the Schiff
base ligand may be assigned to the phenolic (C–O) stretching mode,
according to previous assignments. The pyrimidine ring shows character-
istic stretching absorption bands at 3060 cm–1. The phenyl group shows
C–H stretching at 3030 cm–1 and C=C stretching at 1540 cm–1. The bands
at 1590 cm–1 can be very safely assigned to n(C=N) (pyrimidine).[10]
Strong bands at 1691–1646 and 1622 cm–1 in the IR spectra of the free
ligand assigned to n(C=O)[15] and n(C=N)[11,15,16] are shiffed by 10–30
cm–1 in the spectra of complexes, indicating coordination through the
azomethine nitrogen, phenolic oxygen and carbonyl oxygen of the Schiff
base (Figure 2). In the spectra of a metal complex such as that of Ni(II),
the band at 1273 cm–1 for the phenolic group did not shift, suggesting that
this oxygen atom of the phenolic group is not coordinated to the metal
ion.[15,16] In the spectra of the Cu(II), Ni(II), Co(II) and Zn(II) complexes,
the bands observed in the 495–476 and 420–439 cm–1 region may be due
to n(M–N) and n(M–O), respectively,[13] suggesting that they are bidentate
complexes with the oxygen atom of the carbonyl group and the nitrogen
Figure 3. Suggested structures of the octahedral complexes of the ligand LH2.

1754
So¨nmez, Levent, and ꢀSekerci
atom of the azomethine group coordinated to the metal ion (Figure 3).
Broad bands of the Cu(II), Ni(II), Co(II) and Zn(II) complexes in the
3240–3350 cm–1 region are assigned to the n(OH) vibration of water
molecules.[13]
Proton Nuclear Magnetic Resonance Spectra
1
Deuterated chloroform was used as a solvent to measure the H NMR
spectra of the ligand and its Zn(II) complex but not those of Cu(II), Co(II)
and Ni(II), because of their paramagnetic behaviour. The sharp singlet
observed at about d 10.43 and 12.55 ppm is assigned to the phenolic
protons of the ligand. The singlets at d 9.56 ppm and 8.33 ppm, respectively,
are assigned to the azomethine proton and the pyrimidine ring (C–H) proton
in the spectrum of the ligand. In the spectrum of the Schiff base, the phenyl
multiplet was observed between at d 6.89–7.71 ppm. The 1H NMR spectra of
Zn(II) complex shows approximately the same peaks as those of the free
ligand with the exception that the peak due to the (2-OH) phenolic group
resonance is absent. This is considered to be additional evidence for the
deprotonation of the phenolic OH group.
Electronic Spectra and Magnetic Measurements
The electronic absorption data of the compounds, which were measured
in DMF, are given in Table 2. Because the complexes are insoluble in all of
the other polar organic solvents, the spectra were recorded in DMF as
solvent. In the spectrum of the ligand, the bands in the 390–348 nm range
are assigned to the n ! p* transitions of the azomethine group. During the
formation of the complexes, these bands are shifted to lower wavelength,
suggesting that the nitrogen atom of the azomethine group is coordinated to
the metal ion. The values in the 300–250 nm range are attributed to the
p! p* transition of the aromatic and pyrimidine rings. In the spectra of the
complexes, these bands are shifted slightly to lower wave length.
The electronic spectrum of the Zn(II) complex has bands in the 280–
250 nm range and these bands may be due to the n !p* and p !p*
transitions of the benzene and pyrimidine rings as well as the azomethine
group. In the spectra of the other complexes, the less intense and broad
bands in the 400–260 nm range result from the overlap of the low-energy
p! p* transitions which are mainly localized within the imine chromo-
phore and the LMCT (ligand to metal charge-transfer bands) transition from
the lone pairs of the phenolate oxygen donor to the M(II) ions.
The Cu(II) complex exhibits a tetragonally distorted octahedral ge-
ometry. It shows intense absorption bands in the 298 and 367 nm ranges

Complexes of a Schiff Base
1755
which can be assigned to the p! p* transition of the azomethine group and
charge-transfer bands, respectively. The electronic spectrum of the complex
2
exhibits an absorption band in the range 743 nm, attributed to2 Eg ! T2g
transition suggesting a distorted octahedral geometry. The other bands in
2
2
the range 590 and 497 nm can be assigned to the transitions: B1g ! B2g
2
2
and B1g ! Eg in order of increasing energy. But generally, such chelates
exhibit a broad, structureless band with or without a shoulder between 715–
520 nm depending upon the strength of the field of the ligand. The obtained
value of the effective magnetic moment (2.2 B.M.) is typical for distorted
octahedral Cu(II) chelates.
[Ni(LH2)2Cl2]ꢀ2H2O shows d-d transitions at 517 and 673 nm cor-
3
3
3
3
responding to A2g ! T1g(F) and A2g ! T2g(F), respectively, which
suggests octahedral geometry. The magnetic moment values for the Ni(II)
complex of the Schiff base ligand at room temperature was found to be
3.40 B.M. value is in the normal range (2.8–3.8 BM).[19]
The magnetic moment values for the [Co(LH)2] complex is near the
spin-only value for high-spin octahedral complexes. The electronic spec-
1
4
trum shows two bands at 760 and 523 nm attributed to T1g ! A2g (n2) and
4
4T1g(F) ! T1g(P) (n3) transitions, respectively, in an octahedral geometry
around the Co(II) ion.[19] The band observed at 261–357 nm is assigned to
the p !p* transition of the azomethine group and charge-transfer bands.
The Zn(II) complex is diamagnetic as expected for its d10 configuration.
The metal-to-ligand ratio of all the complexes was found to be 1:2. The
Zn(II) and Cu(II) complexes have, respectively, one and two additional
molecules of water of crystallization. The metal-to-ligand ratio of the Ni(II)
complex was found to be 1:2, in addition to two chloride ligands and two
additional molecules of water of crystallization.
Molar conductance value of the Ni(II) complex is 17.00 O–1 cm2
mole–1. The Ni(II) complex, which contains coordinated chloride ions, is
non-conducting or shows an increasing degree of conductivity with time
which would be due to their replacements by DMF solvent molecules.[2,9]
The other complexes were non-electrolytes.
Single crystals of the complexes could not be isolated from any
solutions, thus no definitive structure can be described. However, the an-
alytical, spectroscopic and magnetic data enable us to suggest possible
structures as shown in Figure 3.
Thermal Studies
The thermal stability of the complexes was investigated using thermal
gravimetric analysis. The TGA curves were obtained at a heating rate of
10 °C/min. in N2 atmosphere over the temperature range at 30–850.0 °C.

1756
So¨nmez, Levent, and ꢀSekerci
The Cu(II) complex was stable up to 32.0 °C and its decomposition
started at this temperature and was completed at 551.0°C. The Cu(II)
complex decomposed and produced CuO as residue [calculated (found) %:
8.65 (9.10)] in three steps in the temperature ranges 32.0–220.0, 220.0–
449.0 and 449.0–551.0 °C. In the decomposition process of the Cu(II)
complex, the mass losses corresponded to H2O, Ph-C=O- and the other
organic moieties leaving in the first, second and third stages of the de-
composition, respectively. The three stages of the decomposition of the
Cu(II) complex were irreversible.
The Ni(II) complex was stable up to 38.0 °C and its decomposition
started at this temperature and was completed at 672.0 °C. The Ni complex
decomposed and produced NiO as residue [found (calculated) %: 9.16
(7.56)] in four steps in the temperature ranges 38.0–148.0, 148.0–280.0,
280.0–592.0 and 592.0–672.0 °C. In the decomposition process of the
Ni(II) complex, the mass losses corresponded to H2O, Cl, Ph and the other
organic moieties leaving in the first, second, third and fourth stages of the
decomposition, respectively. The four stages of decomposition of Ni(II)
complex were irreversible.
The Co(II) complex was stable up to 68.0 °C and its decomposition
started at this temperature and was completed at 570.0 °C. The Co(II)
complex decomposed and produced CoO as residue [found (calculated) %:
8.68 (8.52)] in three steps in the temperature ranges 68.0–270.0, 270.0–
443.0 and 443.0–570.0 °C. In the decomposition process of the Co(II)
complex, the mass losses corresponded to H2O, Ph-C=O- and other
organic moieties leaving in the first and second stages of the decomposi-
tion, respectively. The two stages of the decomposition of the Co(II) com-
plex were irreversible.
The Zn(II) complex was stable up to 30.0 °C and its decomposition
started at this temperature and was completed at 590.0 °C. The Zn(II)
complex decomposed and produced ZnO as residue [found (calculated) %:
10.02 (9.01)] in three steps in the temperature ranges 30.0–260.0, 260.0–
478.0 and 478.0–590.0 °C. In the decomposition process of the Zn(II)
complex, the mass losses corresponded to H2O, Ph-C=O- and the other
organic moieties leaving in the first, second and third stages of the de-
composition, respectively. The three stages of decomposition of the Zn(II)
complex were irreversible.
The Co(II) complex is thermally stable up to 68.0 °C. In the TGA
curve of the Zn(II) complex, 1.99% weight loss was observed at 260.0 °C.
In the TGA curve of the Cu(II) complex, 3.92% weight loss was observed
at 220.0 °C. In the TGA curve of the Ni(II) complex, 3.64% weight loss
was observed at 148.0 °C. These observations show that the complexes
contain 1, 2 and 1 mols of water of crystallization per complex molecule,

Complexes of a Schiff Base
1757

1758
So¨nmez, Levent, and ꢀSekerci
respectively. The IR spectra of the complexes include a broad band in the
region 3245–3360 cm–1 due to the n(O–H) frequency of water of crys-
tallization.[14–18,20] This water content was also identified by the elemental
analyses. This decomposition process of the Cu(II), Ni(II), Co(II) and Zn(II)
complexes was also confirmed by TGA data. As can be seen in Table 3, the
most stable complex is the Co(II) complex. The weight losses for the
Cu(II), Ni(II) Co(II) and Zn(II) complexes were found to be approximately
the same, when expressed as the percentages calculated stoichiometrically
from their chemical formulas given in Tables 1 and 3. All of these com-
plexes undergo complete decomposition to the corresponding metal oxides,
CuO, NiO, CoO or ZnO[14–16,21–36] (Table 3).
CONDUCTIVITY
The complexes are non-electrolytes as shown by their molar conductivity
(AM) in DMF, which are in the range[2,8,14–36] 1.5–17.0 O–1 cm2 mol–1
.
ACKNOWLEDGMENT
We thank the Research Fund of the Yu¨zu¨ncu¨ Yıl University for fi-
nancial support.
REFERENCES
1. Tenor, E.; Ludwig, R. Bioactivity of copper and zinc complexes of
Schiff bases derived from salicylaldehyde or acetylacetone. Pharmazie
1971, 26, 534–539.
2. Calligaris, M.; Randaccio, L. Comprehensive Coordination Chemistry;
Wilkinson, G., Ed.; Pergamon Press, 1987; 2, 725.
3. Casellato, U.; Vigato, P.A. Transition metal complexes with binucleat-
ing ligands. Coord. Chem. Rev. 1977, 23, 31–117.
4. Ayat, M.I.; Sallam, S.A.; Maabrouk, H.E. Characterisation and thermal
behaviour of Cu(II) chelates of Schiff bases derived from aminopy-
ridines. Thermochim. Acta 1991, 189, 65–73.
5. Szlyk, E.; Biniak, S.; Larsen, E. Electrochemical and electrocatalytic
studies of the N,N’-(1R,2R)-( ꢁ )-1,2-cyclohexylenebis(salicylidene-
iminato)cobalt(II) complex. J. Solid State Electrochem. 2001, 5, 221–
226.

Complexes of a Schiff Base
1759
6. Raman, N.; Kulandaisamy, A.; Shunmugasundaram, A.; Jeyasubrama-
nian, K. Synthesis, spectral, redox and antimicrobial activities of
Schiff base complexes derived from 1-phenyl-2,3-dimethyl-4-amino-
pyrazol-5-one and acetoacetanilide. Transit. Met. Chem. 2001, 26,
131–135.
7. Zigi, G.; Zhenhuan, Y. Synthesis and characterization and anticancer
activity of L-alanin Schiff base complexes of Cu(II), Zn(II), Ni(II) and
Co(II). Synth. React. Inorg. Met.-Org. Chem. 1992, 20, 335–344.
8. Zishen, W.; Zhiping, L.; Zhenhuan, Y. Synthesis and characterization of
Cu(II), Zn(II), Ni(II) and Co(II) 4-hydroxysalicylaldehyde. Transit. Met.
Chem. 1993, 18, 291.
9. J Ferreira, R.; Ben-Zui, E.; Yamane, T.; Vasilenlas, J.; Davitson, N.
Advances in the Chemistry of Coordination Compounds; Krischner, S.,
Ed.; New York, 1961.
10. Akc¸amur, Y.; Altural, B.; Sarıpınar, E.; Kollenz, G. A simple synthesis
of functionalized 1H pyrimidines. Reaction of cyclic oxalyl compound.
Monatsh. Fu¨r Chem. 1989, 120, 1015–1020.
11. So¨nmez, M. Synthesis and characterization of copper(II), nickel(II),
cadmium(II), cobalt(II) and zinc(II) with 2-benzoyl-3-hydroxy-1-
naphthylamino-3-phenyl-2-propen-1-one. Tu¨rk. J. Chem. 2001, 25,
181–185.
12. So¨nmez, M. Synthesis and characterization of copper(II), nickel(II),
cadmium(II), cobalt(II) and zinc(II) with 2-benzoyl-3-hydroxy-1-
naphthylamino-3-phenyl-2-propen-1-one. Chem. Abstr. 2001, 135,
189255.
13. Bellamy, L.J. The Infrared Spectra of Complex Molecules; Chapman
and Hall: London, 1978.
˙
14. Temel, H.; Ilhan, S.; ꢀSekerci, M.; Ziyadanog˘ulları, R. Synthesis and
characterization of new Cu(II), Ni(II), Co(II) and Zn(II) complexes with
Schiff base. Spectrosc. Lett. 2002, 35, 219–228.
15. So¨nmez, M.; ꢀSekerci, M. Synthesis and characterization of Cu(II),
Co(II), Ni(II) and Zn(II) Schiff base complexes from 1-amino-5-
benzoyl-4-phenyl-1H-pyrimidine-2-one with salicylaldehyde. Pol. J.
Chem. 2002, 76 (7), 907–914.
16. So¨nmez, M.; ꢀSekerci, M. Synthesis and characterization of Cu(II),
Co(II), Ni(II) and Zn(II) Schiff base complexes from 1-amino-5-
benzoyl-4-phenyl-1H-pyrimidine-2-one with salicylaldehyde. Chem.
Abstr. 2002, 137, 225752.
17. ꢀSekerci, M.; Alkan, C.; C¸ ukurovalı, A. Synthesis and metal complexa-
tion of a Schiff base derivative of 2-amino-4-(p-tolyl)thiazole. Russ. J.
Inorg. Chem. 2000, 45, 1229.

1760
So¨nmez, Levent, and ꢀSekerci
18. ꢀSekerci, M.; Alkan, C.; C¸ ukurovalı, A. Synthesis and metal complexa-
tion of a Schiff base derivative of 2-amino-4-(p-tolyl)thiazole. Chem.
Abstr. 2000, 134, 12739.
19. Lever, A.B.P. Inorganic Electronic Spectroscopy; Elsevier: Amster-
dam, 1984.
20. Temel, H.; Sꢀekerci, M. Novel complexes of mangenese(II),
cobalt(II), copper(II) and zinc(II) with Schiff base derived from
1,2-bis( p-aminophenoxy)ethane and salicylaldehyde. Synth. React.
Inorg. Met.-Org. Chem. 2001, 31, 849.
21. ꢀSekerci, M.; Tas¸, E. The synthesis and characterization of 1,2-O-
cyclohexylideneaza-8-aminooctane and some of its transition metal
complexes. Heteroat. Chem. 2000, 11, 254.
22. ꢀSekerci, M. The synhesis and Co(II), Cu(II) and Ni(II) complexes of 4-
(2,4-diaminobutyl)-2-phenyl-1,3-dioxolane. Synth. React. Inorg. Met.-
Org. Chem. 2000, 30, 117.
23. ꢀSekerci, M. Synthesis, magneto-spectral and thermal studies of
cobalt(II), nickel(II) and copper(II) coplexes of new unsymmetrical
1,2-dihydroxyimino-3,8-diaza-9-phenylnonane. Russ. J. Inorg. Chem.
2000, 45, 1525.
24. ꢀSekerci, M. Synthesis, magneto-spectral and thermal studies of
cobalt(II), nickel(II) and copper(II) coplexes of new unsymmetrical
1,2-dihydroxyimino-3,8-diaza-9-phenylnonane. Chem. Abstr. 2001,
134, 320151.
25. ꢀSekerci, M.; Alkan, C. The synthesis and characterization of Co(II),
Ni(II), Cu(II) and UO2(VI) complexes of 1,2-O-benzalaza-aminohep-
tane. Synth. React. Inorg. Met.-Org. Chem. 1999, 29, 1685.
26. ꢀSekerci, M. The synthesis and Co(II), Ni(II), Cu(II) and UO2(VI)
complexes of new amine-containing 1,3-dioxolane. Russ. J. Inor. Chem.
1999, 44, 1147.
27. ꢀSekerci, M. The synthesis and Co(II), Ni(II), Cu(II) and UO2(VI)
complexes of new amine-containing 1,3-dioxolane. Chem. Abstr. 1999,
132, 29922.
28. ꢀSekerci, M. Synthesis and complexation of new unsymmetrical 1,2-
dihydroxyimino-3,6-diaza-7-phenylheptane. Russ. J. Inorganic Chem.
2000, 45, 59.
29. ꢀSekerci, M. Synthesis and complexation of new unsymmetrical 1,2-
dihydroxyimino-3,6-diaza-7-phenylheptane. Chem. Abstr. 2000, 132,
317219.
30. ꢀSekerci, M. The synthesis and characterisation of a new symmetrical
8,9-bis(hydroxyimino)-4,7,10,13-tetraaza-1,2,15,16-O-dicyclopentyli-
denehexadecane and its transition metal complexes. S. Afr. J. Chem.
1999, 52, 79.

Complexes of a Schiff Base
1761
31. ꢀSekerci, M. The synthesis and characterisation of a new symmetrical
8,9-bis(hydroxyimino)-4,7,10,13-tetraaza-1,2,15,16-O-dicyclopentyli-
denehexadecane and its transition metal complexes. Chem. Abstr. 1999,
132, 87287.
32. ꢀSekerci, M. Synthesis and complexation of new unsymmetrical 1,2-
dihydroxyimino-3,7-diaza-8-phenyloctane. Synth. React. Inorg. Met.-
Org. Chem. 1999, 29, 487.
33. Sꢀekerci, M. Spectrophometric studies, shynthesis and magnetic
properties Co(II), Ni(II), Cu(II) and UO2(VI) complexes of 1,2-O-iso-
propylidene-4-aza-7-aminoheptane. Russ. J. Inor. Chem. 2000, 45,
1348.
34. Sꢀekerci, M. Spectrophometric studies, shynthesis and magnetic
properties Co(II), Ni(II), Cu(II) and UO2(VI) complexes of 1,2-O-iso-
propylidene-4-aza-7-aminoheptane. Chem. Abstr. 2000, 134, 94687.
35. ꢀSekerci, M. Sythesis of (Z,Z)-1,2-dihydroxyimino-3,6-diamino-8,9-
O,O-cyclo pentylidene-nonane-8,9-diol and its complexes with cop-
per(II), nickel(II), cobalt(II) and uranyl(VI). Synth. React. Inorg. Met.-
Org. Chem. 2000, 30, 191.
¨
36. C¸ ukurovalı, A.; Yılmaz, I.; Ahmedzade, M.; Ozmen, H. A new
cyclobutane-substituted Schiff base ligand and its Co(II), Cu(II), Ni(II)
and Zn(II) complexes. Synth. React. Inorg. Met.-Org. Chem. 2001, 31,
255.
Received December 13, 2002
Accepted July 1, 2003
Referee I: G. A. Brewer
Referee II: R. H. Gayhart