Synthesis and characterization of some cobalt(II), copper(II), and nickel(II) complexes with new schiff bases from the reaction of p-aminoazobenzene with salicylaldehyde

Article abstract of DOI:10.1081/SIM-120037512

Two new Schiff bases have been synthesized by the reaction of p-aminoazobenzene with salicylaldehyde (L¹H) and the oxidative polycondensation product of L¹H (L²H₂). The complexes of cobalt(II), copper(II), and n

Full text of DOI:10.1081/SIM-120037512

This article was downloaded by: [University of Arizona]
On: 22 May 2013, At: 15:23
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer
House, 37-41 Mortimer Street, London W1T 3JH, UK
Synthesis and Reactivity in Inorganic and Metal-
Organic Chemistry
Publication details, including instructions for authors and subscription information:
http://www.tandfonline.com/loi/lsrt19
Synthesis and Characterization of Some Cobalt(II),
Copper(II), and Nickel(II) Complexes with New Schiff
Bases from the Reaction of p‐Aminoazobenzene with
Salicylaldehyde
Esin Peker a & Selahattin Serin b
a Department of Chemistry, Faculty of Science and Arts, Kahramanmaraş Sütçü İmam
University, Kahramanmaraş, Turkey
b Department of Chemistry, Faculty of Science and Arts, Çukurova University, 01133,
Balcalı, Adana, Turkey
Published online: 16 Nov 2010.
To cite this article: Esin Peker & Selahattin Serin (2004): Synthesis and Characterization of Some Cobalt(II), Copper(II),
and Nickel(II) Complexes with New Schiff Bases from the Reaction of p‐Aminoazobenzene with Salicylaldehyde, Synthesis
and Reactivity in Inorganic and Metal-Organic Chemistry, 34:5, 859-872
To link to this article: http://dx.doi.org/10.1081/SIM-120037512
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/terms-and-conditions
This article may be used for research, teaching, and private study purposes. Any substantial or systematic
reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to
anyone is expressly forbidden.
The publisher does not give any warranty express or implied or make any representation that the contents
will be complete or accurate or up to date. The accuracy of any instructions, formulae, and drug doses
should be independently verified with primary sources. The publisher shall not be liable for any loss, actions,
claims, proceedings, demand, or costs or damages whatsoever or howsoever caused arising directly or
indirectly in connection with or arising out of the use of this material.

SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY
Vol. 34, No. 5, pp. 859–872, 2004
Synthesis and Characterization of Some
Cobalt(II), Copper(II), and Nickel(II)
Complexes with New Schiff Bases from
the Reaction of p-Aminoazobenzene
with Salicylaldehyde
Esin Peker1 and Selahattin Serin2,
*
1Department of Chemistry, Faculty of Science and Arts, Kahramanmaras¸
˙
Su¨tc¸u¨ Imam University, Kahramanmaras¸, Turkey
2Department of Chemistry, Faculty of Science and Arts, C¸ ukurova
University, Balcalı, Adana, Turkey
ABSTRACT
Two new Schiff bases have been synthesized by the reaction of p-aminoazo-
benzene with salicylaldehyde (L1H) and the oxidative polycondensation pro-
duct of L1H (L2H2). The complexes of cobalt(II), copper(II), and nickel(II)
with L1H and L2H2 have been prepared. The ligands and their complexes
havebeencharacterizedbyelementalanalyses, IRspectra, electronicabsorp-
tion spectra, mass spectra, 1H and 13C NMR spectra, and magnetic suscepti-
bility measurements. The thermal properties of all complexes have been
*
Correspondence: Selahattin Serin, Department of Chemistry, Faculty of Science and
Arts, C¸ ukurova University, 01133 Balcalı, Adana, Turkey; E-mail: serin@cu.edu.tr.
859
DOI: 10.1081/SIM-120037512
0094-5714 (Print); 1532-2440 (Online)
www.dekker.com
Copyright # 2004 by Marcel Dekker, Inc.

ORDER
REPRINTS
860
Peker and Serin
studied by TG and DTA. The analytical data show that the metal to ligand
ratio in the L1H complexes is 1 : 2, but in the L2H2 complexes it is 1 : 1.
Key Words: p-Aminoazobenzene; Schiff bases; Salicylaldehyde;
Hydroquinones.
INTRODUCTION
Apart from their purely chemical interest, azo-azomethine dyes are being
increasingly used in the textile, leather, and plastic industries.[1] Regarding the
industrial importance of metallized azo dyes relative to their structures, they
can be classified into two main types: those in which the azo group participates
in the coordination to the metal ion with formation of the chelate ring and
those in which it is not.[2]
Schiff bases derived from the salicylaldehydes are known as polydentate
ligands, coordinating in deprotonated or neutral forms.[3] Schiff base com-
plexes containing different central metal atoms such as Cu, Ni, Co, and Pd
have been studied in great detail for their various crystallographic features,
enzymatic reactions, steric effects, structure-redox relationships, mesogenic
characteristics, catalysis, magnetic properties, and their important role in the
understanding of the coordination chemistry of transition metal ions. In
some Schiff base metal chelates, it has been shown that minor changes in
the structure of the ligands containing hard/soft donor atoms, e.g., nitrogen,
sulfur and/or oxygen markedly affected the activity of these compounds.[4,5]
It is known that phenol, naphthols, hydroquinone, and aldehydes enter
into an oxidative polycondensation reaction and form polyconjugated com-
pounds. The oligophenols and their derivatives have been used in various
fields, because of their electron structure properties.[6]
In the present paper, the synthesis and characterization of two new Schiff
bases (Fig. 1) and their Co(II), Cu(II), and Ni(II) metal complexes (Fig. 2) are
reported.
EXPERIMENTAL
Materials
.
.
.
The metal salts Co(OAc)2 4H2O, Cu(OAc)2 H2O, and Ni(OAc)2 4H2O,
p-aminoazobenzene and salicylaldehyde were obtained from Fluka. Solvents
were analytical grade and purified by standard procedures.

ORDER
REPRINTS
Complexes with New Schiff Bases
861
Figure 1. Structures of Schiff base ligands.
Physical Measurements
Elemental analyses (C, H, N) were performed using a Carlo Erba 1106
elemental analyzer. Infrared spectra were obtained using KBr discs (4000–
400 cm21) on a Shimadzu 8300 FTIR spectrophotometer. The electronic spectra
in the 200–900 nm range were obtained using THF, EtOH, CHCl3, n-hexane, n-
heptane, and toluene on a Shimadzu UV-160 A spectrophotometer. 1H and 13
C
NMR spectra were taken on a Varian XL-200 NMR instrument. TMS was used
as internal standard and deuterated DMSO as solvent. Magnetic measurements
were carried out by the Gouy method using Hg[Co(SCN)4]ascalibrant. Massspec-
tra of the ligands were recorded on a VG Zab Spec. GC-MS spectrometer with fast
atom bombardment. Thermal analyses were performed on Shimadzu DTA 50 and
TG 50 H models using 10 mg samples. The DTA and TG curves were obtained at a
heating rate of 10 8C min21 in dry N2 atmosphere in the 25–750 8C range.
Synthesis of N-(p-Phenylazobenzene)salicylaldeimine (L1H)
p-Aminoazobenzene (1.97 g, 10 mmol) dissolved in EtOH (10 mL) was
carefully added with stirring to a solution of salicylaldehyde (1.22 g,
10 mmol) in EtOH (10 mL). The resulting mixture was allowed to stir magnet-
ically under reflux for 2–3 hr. After cooling the resulting precipitate was
filtered, washed with cold EtOH, recrystallized from EtOH, and dried in a
vacuum dessicator. Yield: 2.53 g (84 %), M.p.: 160 8C, M.w.: 301 g mol21
.

ORDER
REPRINTS
862
Peker and Serin
Figure 2. Proposed structures of the complexes.
Synthesis of m,m0-di[N-(p-Phenylazobenzene)]-
salicylaldeimine (L2H2)
The ligand L1H (1 g, 3 mmol) was dissolved in EtOH (40 mL). Then 5 mL
of a solution of KOH (0.19 g, 3 mmol) was added with stirring to the solution
of L1H. Subsequently 0.83 mL of an aqueous solution of NaOCl (30%, 0.83 g,
11.10 mmol)[7] was added to the mixture and the solution was allowed to stir

ORDER
REPRINTS
Complexes with New Schiff Bases
863
magnetically for 5 hr. The resulting solution was neutralized with HCl. After
neutralization, the precipitated solid was filtered, washed with water, recrys-
tallized from n-heptane, and dried in a vacuum dessicator.
Synthesis of the Metal Complexes
Cobalt(II) Complex of L1H
.
A solution of Co(OAc)2 4H2O (0.125 g, 0.5 mmol) in MeOH (20 mL)
was added to a solution of the ligand L1H (0.301 g, 1 mmol) in absolute
EtOH (40 mL). The mixture was refluxed for 2–4 hr at 80 8C. The precipitated
compound was filtered, washed with cold EtOH, and dried in vacuo over
P4O10.
Cobalt(II) Complex of L2H2
.
A solution of Co(OAc)2 4H2O (0.125 g, 0.5 mmol) in MeOH (20 mL)
was added to a solution of the ligand L2H2 (0.300 g, 0.5 mmol) in absolute
EtOH (40 mL). The mixture was refluxed for 2–4 hr at 80 8C. The precipitated
compound was filtered, washed with cold EtOH, and dried in vacuo over
P4O10.
Copper(II) Complex of L1H
.
A solution of Cu(OAc)2 H2O (0.100 g, 0.5 mmol) in MeOH (20 mL) was
added to a solution of the ligand L1H (0.301 g, 1 mmol) in absolute EtOH
(40 mL). The mixture was stirred at 80 8C. The precipitated complex was
filtered, washed with cold EtOH, and dried in vacuo over P4O10.
Copper(II) Complex of L2H2
.
A solution of Cu(OAc)2 H2O (0.100 g, 0.5 mmol) in MeOH (20 mL) was
added to a solution of the ligand L2H2 (0.300 g, 0.5 mmol) in absolute EtOH
(40 mL). The mixture was stirred at 80 8C. The precipitated complex was
filtered, washed with cold EtOH, and dried in vacuo over P4O10.
Nickel(II) Complex of L1H
.
A solution of Ni(OAc)2 4H2O (0.124 g, 0.5 mmol) in MeOH (20 mL) was
added to a solution of the ligand L1H (0.301 g, 1 mmol) in absolute EtOH

ORDER
REPRINTS
864
Peker and Serin
(40 mL). The mixture was stirred at 80 8C. The precipitated complex was
filtered, washed with cold EtOH and dried in vacuo over P4O10.
Nickel(II) Complex of L2H2
.
A solution of Ni(OAc)2 4H2O (0.124 g, 0.5 mmol) in MeOH (20 mL) was
added to a solution of the ligand L2H2 (0.300 g, 0.5 mmol) in absolute
EtOH (40 mL). The mixture was stirred at 80 8C. The precipitated complex
was filtered, washed with cold EtOH, and dried in vacuo over P4O10.
RESULTS AND DISCUSSION
In this study, L1H, L2H2 and their Cu(II), Co(II), and Ni(II) metal com-
plexes were synthesized and characterized. The complexes were synthesized
by the general equations shown below.
M(OAc)2 ꢀ xH2O þ 2L1H ꢁ! ½MðL1Þ2ꢂ þ 2AcOH þ xH2O
1
M(OAc)2 ꢀ xH2O þ 2L2H2 ꢁ! ½MðL2Þꢂn þ 2AcOH þ xH2O
n
The physical data and elemental analysis data of the ligands and their
complexes are given in Table 1. These data show that the metal to ligand
ratio in the L1H complexes is 1 : 2, but in the L2H2 complexes it is 1 : 1 and,
consequently, the general formula of the Schiff base complexes are M(L1)2
and (ML2)n. The Schiff base ligands N-(p-phenylazobenzene)salicylaldeimine
(L1H) and m,m0-di[N-(p-phenylazobenzene)] salicylaldeimine (L2H2) were
synthesized in high yields in EtOH. The ligands are stable at room temperature
and soluble in common organic solvents such as EtOH, CHCl3, and MeOH.
1
The H NMR and thin-layer chromotography results show only one isomer
for m,m0-di[N-(p-phenylazobenzene)]salicylaldimine (L2H2). The complexes
are also stable at room temperature and soluble in THF, DMSO, CHCl3 and
but insoluble in n-hexane, n-heptane, benzene, toluene, etc.
Infrared Spectra
The infrared spectral data of the ligands and their complexes are given in
Table 2. In the ligand spectra, both ligands exhibit bands at 3420 and
3055 cm21 that are assignable to n(OH) and n(Ar–CH).[8,9] But in the com-
plexes, the band at 3420 cm21 is absent. The ligands exhibit bands at 1566
and 1591 cm21, which are assigned to the vibration of the N55N group.[1]

ORDER
REPRINTS
Complexes with New Schiff Bases
865

ORDER
REPRINTS
866
Peker and Serin
Table 2. IR spectral data of the ligands and their complexes (cm21, KBr).a
Compound
n(OH)
n(ArC–H) n(CH55N) n(N55N)
n(M–O) n(M–N)
L1H
3,425 m
—
—
3,055 m
3,058 m
3,037 m
3,057 m
3,055 m
3,058 m
3,060 m
3,058 m
1,614 s
1,604 s
1,608 s
1,612 s
1,614 s
1,616 s
1,606 m
1,618 s
1,591 s
1,573 s
1,587 m
1,562 s
1,591 s
1,560 m
1,579 s
1,558 m
—
—
Co(L1)2
Cu(L1)2
Ni(L1)2
L2H2
422 w
418 w
445 m
—
596 m
599 m
563 m
—
—
3,425 m
—
—
(CoL2)n
(CuL2)n
(NiL2)n
418 m
420 w
420 w
607 m
594 m
611 m
—
as, strong; m, medium; w, weak.
The band at 1614 cm21 is due to the vibration of the azomethine group in both
ligands. This band in the complexes is shifted towards lower frequencies as a
result of coordination of the azomethine nitrogen atom to the metal ion.[10] In
the complexes, new weak bands in the 611–520 and 445–418 cm21 range
may be attributed to n(M–N) and n(M–O) stretching.[2,11]
Electronic Spectra
The electronic absorption spectral data[12,13] for the ligands are given in
Table 3 and for the complexes in Table 4. In order to investigate the keto-
amine–enolimine tautomeric forms of the Schiff base ligands, the electronic
spectra are recorded in EtOH, CHCl3, toluene, n-hexane, and n-heptane. As
seen in Table 3, the n ! pꢃ and p ! pꢃ transitions of L1H in non-polar sol-
vents such as toluene, n-hexane, and n-heptane were observed at 373, 348, and
335 nm, respectively. The same transitions in polar solvents such as CHCl3
and EtOH, are observed in the 462–432 and 369–348 nm ranges. These
data show that, L1H prefers the tautomeric ketoamine form in non-polar
solvents and the tautomeric enolimine form in non-polar solvents (Fig. 3).
The interaction of enolimine with a hydrogen bond-forming solvent
(EtOH) would presumably reduce the O–H bond strength and facilitate proton
transfer to the nitrogen center.[14]
For L2H2 the n ! pꢃ and p ! pꢃ transitions in all solvents were
observed at 371–366 and 348 nm. These data show that L2H2 prefers the
tautomeric enolimine form in both polar and non-polar solvents. The spectra
of all complexes (Fig. 2, Table 4) contain absorption bands in the 813, 812,
706, and 569 nm ranges, which may be assigned to the d–d transition of
metal ions.[15]

ORDER
REPRINTS
Complexes with New Schiff Bases
867
l
l
l
l
l

ORDER
REPRINTS
868
Peker and Serin
Table 4. UV-VIS and magnetic moment data of the complexes in THF.
Compound
Co(L1)2
lmaxa (1)b
meff (BM)
630 (4,647), 448 (9,294), 361 (97,764), 303 (52,706),
274 (6,411)
4.99
1.65
Cu(L1)2
603 (1,360), 490 (1,560), 361 (30,680), 349 (31,700),
265 (10,350)
Ni(L1)2
(CoL2)n
(CuL2)n
(NiL2)n
539 (185), 490 (1,259), 375 (57,741), 283 (12,519)
812 (118), 422 (9,529), 358 (77,706), 346 (92,706)
706 (40), 394 (23,740), 360 (35,900), 267 (5,660)
813 (4), 385 (7,133), 346 (6,358), 275 (262)
Diamagnetic
5.57
2.21
2.98
aIn nm.
bIn M21, cm21
.
1H and 13C NMR Spectra
In order to better understand the structure of the ligands, 1H and 13C NMR
spectral data in DMSO-d6 as solvent are given in Table 5 and exhibit all
1
expected signals. The H NMR spectra of the ligands exhibit singlet signals
in the 10.7–12.7 and 8.9–8.1 ppm ranges, which are attributed to the OH
group and azomethine group protons, respectively.[16] In the spectra of the
Ni(II) complexes, the singlets which are attributed to the OH groups, are absent
and the signals in the 8.9 and 8.1 ppm ranges, which are attributed to the azo-
methine group protons appear downfield at 8.7 and 9.3 ppm, indicating coordi-
nation of the ligands to the metal ion via the azomethine nitrogen. In L1H,
multiplets at 6.5–7.9 ppm that may be assigned to aromatic ring protons.[17]
In L2H2 there is a singlet for Ha–Ha0 protons in the 6.0 ppm and a doublet
for Hb–Hb0 and Hc–Hc0 protons in the 6.64–6.74 ppm.[18] In the L2H2, multi-
plets at 6.0–7.9 ppm that may be assigned to aromatic ring protons.[17] These
signals and thin-layer chromotography results show only one isomer for L2H2,
with the coupling point being para to the hydroxyl group (Fig. 4).
The 13C NMR spectra of the ligands exhibit singlet signals at 163.30 ppm,
which can be assigned to the azomethine group carbon atoms.[12] In the spec-
tra of the Ni(II) complexes, this signal shifted downfield to the 170.2 ppm
range. The signals due to the carbon atoms of aromatic ring are observed in
the 117–133 ppm range.[19]
Figure 3. Ketoamine-enolimine tautomeric forms of Schiff base ligand (L1H).

ORDER
REPRINTS
Complexes with New Schiff Bases
869
Table 5. The 1H NMR (13C NMR) spectral dataa of the ligands and their nickel
complexes.
CH55N
group
(d,ppm)
OH group
(d, ppm)
Ar–H
(d, ppm)
Hb-Hb0,
Hc-Hc0
Compound
L1H
Ha–Ha0
—
10.7 (s)
12.7 (s)
—
8.9 (s)
(163.3)
8.1 (s)
(163.3)
8.7 (s)
(170.2)
9.3 (s)
(170.2)
6.5–7.9 (m)
(117–133)
6.0–7.6 (m)
(117–133)
6.7–8.1 (m)
(118–133)
6.2–7.9 (m)
(118–133)
—
L2H2
6.0 (s)
—
6.64–6.74 (d)
—
Ni(L1)2
(NiL2)n
—
6.0 (s)
6.65–6.73 (d)
as, singlet; m, multiplet.
Mass Spectra
In the mass spectrum of the ligand L1H, the peak observed at m/z 301
may be assigned to the molecular ion Mþ and the peak at m/z 302 is due to
the [M þ 1]þ1 ion. The most intense peak at m/z 289 corresponds to
Figure 4. The synthesis reaction of L2H2.

ORDER
REPRINTS
870
Peker and Serin
[C6H4–N55N–C6H4–N55CH–C5H4OH]þ, which results from loss of one
carbon atom from the parent ligand.The other important peaks at m/z 273
and m/z 154 correspond to [C6H4–N55N–C6H4–N55CH–C5H5]þ and
[C6H4–N55CH–C5H5]þ resulting from loss of one oxygen and the [C6H4–
N55N]þ fragment.
The dimer ligand L2H2 has been synthesized by the oxidative conden-
sation reaction of L1H. The molecular weight distribution of L2H2 has been
determined by HPLC. Mn (the number of average molar mass) and the Mw
(the weight of average molar mass) values for L2H2 were determined by
HPLC[20] to be 600. As expected the results found for Mn and Mw, were
the same. The polydispersity (Mw/Mn) value for L2H2 is 1. This data
shows that L2H2 contains only dimer units.[21] The elemental analyses are
in agreement with this molecular weight.
The molecular weight distribution of L2H2 metal complexes has been
determined by HPLC. Mn (the number of average molar mass) and the Mw
(the weight of average molar mass) values for L2H2 metal complexes were
analyzed by HPLC and determined to be 6589–6810 (CoL2)n, 6635–6728
(CuL2)n, and 6590–6798 (NiL2)n. The polydispersity (Mw/Mn) values are
1.033 for (CoL2)n, 1.014 for (CuL2)n, and 1.031 for (NiL2)n. These data
show that the L2H2 metal complexes are oligomers.
Magnetic Measurements
Magnetic moment data of the complexes are given in Table 4. The cop-
per(II) complexes exhibit 1.65–2.21 B.M. values suggesting that copper(II)
ion has square-planar geometry.[21] The values of 4.99 and 5.52 B.M. observed
for Co(L1)2 and (CoL2)n reveal tetrahedral geometry around the Co(II) ion.
The nickel(II) complex of L1H is diamagnetic and has square-planar geometry
around the metal center. The magnetic moment of the nickel(II) complex of
L2H2 is 2.98 B.M., which is consistent with a tetrahedral structure.[5]
Thermal Studies
Thermal degradation of the complexes proceeded in two steps. The
first step represents the primary decomposition of the complexes in the
225–300 8C range. The second step within the 600–675 8C range represents
the final decomposition of the complexes to the metal oxides. The thermal
studies of complexes show that there are no water molecules in the
complexes.[5]

ORDER
REPRINTS
Complexes with New Schiff Bases
871
REFERENCES
˙
˘
1. Karaer, H.; Gu¨mru¨kc¸u¨oglu, I.E. Synthesis and spectral characterization of
novel azo-azomethine dyes. Turk. J. Chem. 1999, 23, 67–71.
2. Soliman, E.M.; El-Shabasy, M. Synthesis characterization and electrical
conductivity properties of homo- and heterodi- and trimetalic complexes
of mixed azo dyes. J. Mater. Sci. 1994, 29, 5405–4509.
3. Souza, P.; Garcia-Vazquez, J.A.; Masaguer, J.R. Synthesis and character-
ization of copper(II) and nickel(II) complexes of the Schiff base derived
from 2-(2-aminophenly)benzimidazole and salicylaldimine. Transit. Met.
Chem. 1985, 10, 410–412.
4. Khandar, A.A.; Nejati, K. Synthesis and characterization of a series of
copper(II) complexes with azo-linked salicylaldimine Schiff base ligands.
.
Crystal structure of Cu5PHAZOSALTN CHCl3. Polyhedron 2000, 19,
607–613.
5. Tu¨mer, M.; C¸ elik, C.; Koksal, H.; Serin, S. Transition metal
¨
complexes of bidentate Schiff base ligands. Transit. Met. Chem. 1999,
24, 525.
6. Ragimov, A.V.; Mamedov, A.B.; Gasanova, S.G. New efficient dielectric
and antistatic materials based on oligoaminophenols. Polym. Int. 1997,
43, 343–346.
˙
¨
˘
7. Kaya, I.; Demir, O.; Vilayetoglu, A.R. The synthesis and characterization
of planar oligophenol with Schiff base substitute. Synth. Met. 2002,
126 (2–3), 183–191.
8. Sanmartin, J.; Bermejo, M.R.; Garic¸-Deibe, A.M.; Maneiro, M.; Large, C.;
Costa-Filho, A.J. Mono- and polynuclear complexes of Fe(II), Co(II),
Ni(II), Cu(II), Zn(II) and Cd(II) with N,N-bis(3-hydroxysalicylidene)-
1,3-diamino-2-propanol. Polyhedron 2000, 19, 185–192.
9. Jaworska, J.K. New platinum(II) complexes with Schiff base ligands.
Transit. Met. Chem. 1994, 19, 296–298.
10. Maurya, R.C.; Mishra, D.D.; Jain, S.; Jaiswal, M. Synthesis and charac-
terization of some mixed-ligand complexes of copper(II) and cobalt(II)
with Schiff bases and heterocyclic organic compounds. Synth. React.
Inorg. Met.-Org. Chem. 1993, 23 (8), 1335–1349.
11. El-Saied, F.A.; Ayad, M.I.; Aly, S.A. Tin(IV), titanium(IV) and
hafnium(IV) complexes of some aromatic Schiff bases derived from
4-aminoantipyrine. Transit. Met. Chem. 1993, 18, 279–282.
¨
12. Tu¨mer, M.; Koksal, H.; Serin, S. Synthesis, characterization and
thermal investigation of some metal complexes derived from new Schiff
base ligands. Synth. React. Inorg. Met.-Org. Chem. 1998, 28 (8),
1393–1404.

ORDER
REPRINTS
872
Peker and Serin
13. Zolezzi, S.; Decinti, A.; Spodine, E. Sythesis and characterization of
copper(II) complexes with Schiff base ligands derived from ethylene-
diamine, diphenylethylenediamine and nitro, bromo and methox sali-
cylaldehyde. Polyhedron 1999, 18, 897–904.
˘
¨
14. Tu¨mer, M.; Koksal, H.; Digrak, M.; Serin, S. Antimicrobial activity
studies of mononuclear and binuclear mixed-ligand copper(II) complexes
derived from Schiff base ligands and 1,10-phenanthroline. Transit. Met.
Chem. 1999, 24, 13–17.
¨
15. Tu¨mer, M.; Koksal, H.; Serin, S. Synthesis, characterization and thermal
studies of mononuclear and binuclear complexes of copper(II) with Schiff
bases derived from 1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone. Synth.
React. Inorg. Met.-Org. Chem. 1996, 26 (9), 1589–1598.
¨
16. Tu¨mer, M.; Koksal, H.; S¸ener, K.; Serin, S. Antimicrobial activity studies
of binuclear metal complexes derived from tridentate Schiff base ligands.
Transit. Met. Chem. 1999, 24, 414–420.
17. Parr, J.; Ross, A.T.; Slawin, A.M.Z. Tricoordinate complexes of lead(II)
with innocent Schiff base ligands. Polyhedron 1997, 16, 2765–2770.
˙
˘
18. Kaya, I.; Vilayetoglu, A.R.; Serin, S. The synthesis and properties of
oligosalicylaldehyde and its Schiff base oligomer. Polymer 2001,
42 (11), 4859–4865.
¨
19. Tu¨mer, M.; Koksal, H.; Serin, S. Synthesis and characterization of mono-
nuclear copper(II), cobalt(II) and nickel(II) chelates with new bidentate
aromatic Schiff bases. Synth. React. Inorg. Met.-Org. Chem. 1997,
27 (5), 775–786.
20. Chafi, N.; Kolli, M.; Vergnaud, J-M.; Montheard, J-P. Amines release
from Schiff bases polymers and diffusion from dosage with eudragit RL
in acidic medium. Polym. Sci. 1991, 43, 1837–1847.
21. Ragimov, A.V.; Mamedov, B.A.; Mustafaeva, Sh.I. Oxidative polycon-
densation of 8-oxyquinoline alcoholate. Polymer 1989, 60, 1851–1855.
22. Calvin, M.; Barkelew, C.H. The oxygen-carrying synthetic chelate
compounds. IV. Magnetic properties. J. Am. Chem. Soc. 1946, 68,
2267–2273.
Received December 28, 2001
Accepted February 6, 2004
Referee I: K. Birdwhistell
Referee II: L. J. Kirschenbaum

Request Permission or Order Reprints Instantly!
Interested in copying and sharing this article? In most cases, U.S. Copyright
Law requires that you get permission from the article’s rightsholder before
using copyrighted content.
All information and materials found in this article, including but not limited
to text, trademarks, patents, logos, graphics and images (the "Materials"), are
the copyrighted works and other forms of intellectual property of Marcel
Dekker, Inc., or its licensors. All rights not expressly granted are reserved.
Get permission to lawfully reproduce and distribute the Materials or order
reprints quickly and painlessly. Simply click on the "Request Permission/
Order Reprints" link below and follow the instructions. Visit the
U.S. Copyright Office for information on Fair Use limitations of U.S.
copyright law. Please refer to The Association of American Publishers’
Fair Use in the Classroom.
(AAP) website for guidelines on
The Materials are for your personal use only and cannot be reformatted,
reposted, resold or distributed by electronic means or otherwise without
permission from Marcel Dekker, Inc. Marcel Dekker, Inc. grants you the
limited right to display the Materials only on your personal computer or
personal wireless device, and to copy and download single copies of such
Materials provided that any copyright, trademark or other notice appearing
on such Materials is also retained by, displayed, copied or downloaded as
part of the Materials and is not removed or obscured, and provided you do
not edit, modify, alter or enhance the Materials. Please refer to our
Website
User Agreement for more details.
Request Permission/Order Reprints
Reprints of this article can also be ordered at
http://www.dekker.com/servlet/product/DOI/101081SIM120037512