2,6-Bis((E)-((5-benzoyl-2-thioxo-4-phenylpyrimidin-1(2H)-yl)imino)methyl) -4- (methyl)phenol and its Metal(II) Complexes: Synthesis, spectroscopy, biological activity, and photoluminescence features

Article abstract of DOI:10.1002/zaac.201300224

The preparation, characterization, magnetic measurements, antimicrobial activity, and photoluminescence properties of a number of metal complexes with a Schiff base ligand derived from 2,6-diformyl- 4-methylphenol and 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine- 2-thione are reported herein. UV/Vis spectra and magnetic measurements infer square planar stereochemistry for PdII and PtII complexes, and octahedral arrangement for the other metal complexes. The compounds results in intense emission (where γmax = 402 nm) upon irradiation by UV light. The photoluminescence quantum yields and long excited-state lifetimes of the ligand and its complexes were calculated as 42% and 3.94 ns, respectively. The photoluminescence intensities and quantum yields of metal complexes changed upon complexation with various metal ions. The ligand and its complexes are of interest as organic emitting materials for electroluminescent devices. The complexes were additionally evaluated for in vitro the antimicrobial activity against bacterial and fungal strains. While CuII, CoII, and PtII complexes have good antifungal efficiency against yeast (MICs, 80 μg·mL-1), only the complex [Cu(L)(AcO)]·4H ₂O had effective and selective antimicrobial activity against all tested microorganisms with MIC values in the range of 40-80 μg·mL-1, except for E. coli ATCC 4230. This study suggests that the complex [Cu(L)(AcO)]·4H₂O may be a new potential antimicrobial substance towards bacteria and fungi.

Full text of DOI:10.1002/zaac.201300224

Job/Unit: Z13224
/KAP1
Date: 14-08-13 15:52:18
Pages: 9
ARTICLE
DOI: 10.1002/zaac.201300224
2,6-Bis((E)-((5-benzoyl-2-thioxo-4-phenylpyrimidin-1(2H)-yl)imino)methyl)-4-
(methyl)phenol and its Metal(II) Complexes: Synthesis, Spectroscopy,
Biological Activity, and Photoluminescence Features
Mehmet Gulcan,*[a] Hüseyin Zengin,[b] Metin Çelebi,[a] Mehmet Sönmez,[b] and
[c]
˙
Ismet Berber
Keywords: Schiff bases; Metal complexes; Luminescence; N-Aminopyrimidine-2-thione; Antimicrobial agents
Abstract. The preparation, characterization, magnetic measurements, and quantum yields of metal complexes changed upon complexation
antimicrobial activity, and photoluminescence properties of a number with various metal ions. The ligand and its complexes are of interest
of metal complexes with a Schiff base ligand derived from 2,6-difor- as organic emitting materials for electroluminescent devices. The com-
myl-4-methylphenol and 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine- plexes were additionally evaluated for in vitro the antimicrobial ac-
2-thione are reported herein. UV/Vis spectra and magnetic measure-
tivity against bacterial and fungal strains. While CuII, CoII, and PtII
ments infer square planar stereochemistry for PdII and PtII complexes, complexes have good antifungal efficiency against yeast (MICs,
and octahedral arrangement for the other metal complexes. The com-
pounds results in intense emission (where λmax = 402 nm) upon irradia-
tion by UV light. The photoluminescence quantum yields and long
80 μg·mL–1), only the complex [Cu(L)(AcO)]·4H2O had effective and
selective antimicrobial activity against all tested microorganisms with
MIC values in the range of 40–80 μg·mL–1, except for E. coli ATCC
excited-state lifetimes of the ligand and its complexes were calculated 4230. This study suggests that the complex [Cu(L)(AcO)]·4H2O may
as 42% and 3.94 ns, respectively. The photoluminescence intensities
be a new potential antimicrobial substance towards bacteria and fungi.
Complexes of macrocyclic ligands derived from 2,6-
diformyl-4-methylphenol are of great interest because they can
mimic the structural features of macrocyclic biological mole-
cules.[6–8] Planar ligands with amine or imine donor groups
and bridging phenolic oxygen atoms are referred to as Robson-
type ligands. The Robson-type ligands are usually obtained by
condensation of appropriate formyl and amine precursors. In
our case, we have used a pyrimidine derivative, giving as a
result a compartmental type ligand.[9]
The search for new organic materials for light emitting de-
vices has attracted much attention in recent years.[10–12] For
example, organic polymers, which exhibit strong luminescence
at low driving voltages, in particular those that emit in the blue
region, are of great interest for flat panel display applica-
tions.[13,14]
Introduction
The role of Schiff bases in coordination chemistry has been
extensively studied and quite satisfactory explained. Schiff
bases can be considered as useful chelating agents due to their
ability to encapsulate metal ions into their coordinating moiety
when a suitable functional group, e.g. OH, SH, etc., is present
sufficiently close to the azomethine group.[1,2]
The high stability of Schiff base complexes with different
oxidation states extended the application of these compounds
in a wide range.[3] Schiff base ligands containing various donor
atoms (like N, O, S, etc.) show broad biological activity and
are of special interest because of the variety of ways in which
they are bonded to the transition metal ions.[4,5]
Rare earth complexes with low molecular weight organic
ligands have also been extensively studied to obtain highly
fluorescent materials for application in electroluminescent de-
vices[15,16] and laser systems.[17] Further, numerous aromatic
amines and polymeric arylamines have also been developed as
hole transport layers in organic electroluminescent re-
search.[18,19] The synthesis, luminescence, and cyclic voltam-
metric studies of novel dinuclear ruthenium(II) complexes
have been reported by Yang et al.[20] Fluorescent vic-dioxime-
type ligand and its mono- and dinuclear complexes have been
studied[21] and they reported that the fluorescence emission in-
tensity of ligand decreases dramatically depending on complex
formation with the transition metal ions. This decrease in emis-
* Assist. Prof. M. Gulcan
Fax: +90-4322251806
E-Mail: mehmetgulcan65@gmail.com
[a] Department of Chemistry
Faculty of Science
Yuzuncu Yil University
Van, 65080, Turkey
[b] Department of Chemistry
Faculty of Science and Arts
Gaziantep University
Gaziantep, 27310, Turkey
[c] Department of Biology
Faculty of Science and Arts
Sinop University
Sinop, 57000, Turkey
Supporting information for this article is available on the WWW
under http://dx.doi.org/10.1002/zaac.201300224 or from the au-
thor.
Z. Anorg. Allg. Chem. 0000, ᭿,(᭿), 0–0
© 0000 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
1

Job/Unit: Z13224
/KAP1
Date: 14-08-13 15:52:18
Pages: 9
M. Gulcan et al.
ARTICLE
sion intensities is due to the formation of the coordination which indicative of an octahedral environment around the
complex of nitrogen atom on the ligand with the metal ions.
metal ion.[25,26] The magnetic moment of the NiII complex was
In this paper, we report the synthesis, characterization, and 2.51 µB.
optical properties of a novel Schiff base ligand and its metal
The magnetic moment (2.62 µB) of the CoII complex was
complexes. This ligand and its complexes were found to exhi- lower than the spin-only value (3.87 µB) and the values re-
bit photoluminescence, emitting an intense light upon UV irra- ported for octahedral complexes. The electronic spectra of CoII
diation. The ligand and its transition metal complexes were complex showed two d–d bands at 554 and 476 nm, which and
characterized using photoluminescence spectrophotometry were assigned[8] to the transitions 4T1gǞ4A2g and
(PL) as well as UV/Vis and FT-IR spectroscopy. The structures 4T1g(F)Ǟ4T1g(P) for octahedral arrangement.
1
of ligand and its metal complexes were analyzed by H and
The electronic spectrum of the MnII complex showed bands
13C NMR spectroscopy, API-ES mass spectrometry, and ele- in the region 464–528 nm due to A1gǞ4T1g (4G) (ν1),
mental analysis. The antimicrobial activities of these com- 6A1gǞ4Eg (4G) (ν2), A1gǞ4T2g (4D) (ν3), A1gǞ4T1g (4P)
6
6
6
pounds were also investigated.
(ν4) transitions, respectively, indicating octahedral arrange-
ment.[27] The magnetic moment for the MnII complex was
found to be 5.82 µB, which was in the expected range of octa-
hedral arrangement around the central metal ion.
Results and Discussion
The electronic spectra of PdII and PtII complexes showed
three d–d spin allowed transitions from the three lower lying
“d” levels to the empty dx2–y2 orbital. The bands are attributed
The analytical and physical data of the Schiff base ligand
and their corresponding transition metal complexes are listed
in the Experimental Section. The modes of binding of the
Schiff base to the metal ions were elucidated by comparison
of the FT-IR spectra of the complexes with those of the free
ligand. The complexes were also investigated by elemental
analyses and different spectroscopic methods. A variety of mo-
nonuclear complexes were obtained from the tri-, or pentadent-
ate forms of the ligand.
The obtained complexes were stable in air and had different
melting points. They were insoluble in organic solvents such
as acetone, diethyl ether, and chloroform, but soluble in DMF
and DMSO. The molar conductivity measurements of the solu-
ble complexes in DMF showed values in the range of 4.54–
23.20 Ω–1·cm2·mol–1 indicating non-electrolytes.[22]
1
1
1
to A1gǞ1A2g, A1gǞ1B1g and to A1gǞ1Eg transitions.[25]
FT-IR Spectroscopy
The IR spectra of the free Schiff base ligand and its com-
plexes exhibited several bands in the region 400–4000 cm–1.
To study the binding mode of the ligand in the metal com-
plexes, the IR spectra of the complexes were compared with
that of the free ligand. The IR spectrum of the ligand showed
a ν(C=N) band at 1593 cm–1 and the absence of ν(C=O) at ca.
1680 cm–1 and ν(NH2) bands around 3250–3300 cm–1 because
of Schiff base condensation. The absorption band at 1659 cm–1
is assigned to the benzoyl ν(C=O) moiety. The IR spectrum
of the Schiff base ligand showed a broad band at 3444 cm–1
due to ν(OH). The broadness of the band was attributed to the
Electronic Absorption Spectroscopy and Magnetic
Measurements
The electronic spectra of the ligand and its complexes were presence of an internal OH···N=C hydrogen bond.[28] All solid
recorded in DMF. The significant electronic absorption bands, complexes exhibited broad bands around 3400–3550 cm–1,
molar conductivity, and magnetic susceptibility values of the which were attributed to ν(O–H) of water of crystalli-
ligand and the complexes are shown in the Experimental Sec- zation,[29,30] the existence of it was also proved by elemental
tion. In the UV/Vis region, the compounds show a strong band analyses. The pyrimidine ring showed a characteristic stretch-
at approximately 450–460 nm, which is attributed to intramo- ing absorption band at 3056 cm–1. The strong bands at
lecular charge transfer transition[23] from the π orbital on the 1355 cm–1 and 1593 cm–1 in the IR spectra of the free ligand
phenolate oxygen to the empty d orbitals of the metal.
assigned to ν(C–O) and ν(C=N)[30] that change in the FTIR
The CuII complex of pentadentate HL was found to have an spectra of all complexes, indicating coordination through azo-
acetate group in the coordination sphere. The electronic spec- methine nitrogen and phenol oxygen atoms of the Schiff base.
trum of the CuII complex displays a low energy weak band at The ν(C=S) bands at 1245 and 739 cm–1[4,5,31] in the free li-
516 nm and a strong high energy band at 462 nm. The low- gand are shifted to higher frequency upon complexation, due
energy band in this position is typically expected for an octahe- to coordination with nitrogen atoms of azomethine, oxygen
dral configuration and may be assigned to 10 Dq correspond- atoms of hydroxyl, and sulfur atoms of thione groups. On the
2
ing to the transition EgǞ2T2g. Furthermore, the strong high- other hand, the ν(C=N) azomethine and ν(C–O) bands in the
energy band is assigned to metal to ligand charge transfer. The spectrum of the PdII and PtII complexes remained at almost
magnetic moment of the CuII complex (1.68 µB) is also indica- 1591–1594 cm–1 and 1355–1353 cm–1, suggesting that the
tive of octahedral arrangement.[24]
C=N and C–O groups do not take part in complexation and
The electronic spectrum of the NiII complex showed three indicating bidentate coordination for the Schiff base through
bands at 456, 590, and 620 nm. The first is due to charge trans- the sulfur atoms of thione and two acetates and chloride anions
fer, the last two bands are assigned to octahedral spin allowed to the metal ion. In the spectra of the complexes, the bands
3
3A2g(F)Ǟ3T2g(F), A2g(F)Ǟ3T1g(F) transitions, respectively, observed in the 420–445 cm–1 and 539–569 cm–1 (except for
2
www.zaac.wiley-vch.de
© 0000 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 0000, 0–0

Job/Unit: Z13224
/KAP1
Date: 14-08-13 15:52:18
Pages: 9
A Schiff Base Ligand and its Metal(II) Complexes
PdII and PtII complexes) region might be due to ν(M–S) and tion and photoluminescence spectra were studied for solutions
ν(M–N), respectively.[30,32,33]
of the ligand, which was excited at 258 nm. The most striking
feature was that the Schiff base ligand resulted in an intense
emission upon irradiation by UV light. The photoluminescence
spectrum of the ligand in DMF is shown in Figure 2. Maxi-
mum luminescent intensity was observed at 402 nm and the
full width at half maximum was 132 nm. The ligand exhibited
a photoluminescence quantum yield of 42% and a long ex-
cited-state lifetime of 3.94 ns. The reason for the high quantum
yields is that the π-electron extensive delocalization forms a
large conjugated system in the ligand structure.
1H and 13C NMR Spectroscopy
The 1H NMR and 13C NMR spectra of the Schiff base ligand
were carried out at room temperature in CDCl3 and
[D6]DMSO, respectively (see Supporting Information).
1
The H NMR spectrum of the ligand showed a signal at δ =
2.39 ppm corresponding to the signals of CH3. The sharp sing-
let observed at about δ = 11.76 ppm was due to the phenolic
proton of the ligand.[8] The singlet signals at δ = 9.28 ppm and
9.08 ppm were due to azomethine proton and pyrimidine ring
(C–H) proton in the spectrum of the ligand, respectively. The
signals corresponding aromatic protons appeared between at
δ = 7.32–7.92 ppm.
The 13C NMR spectrum displayed characteristic signals at
191.97, 176.42, and 165.93 ppm due to the (OC–Ar), (C=S,
pyrimidine) and (–C6, pyrimidine ring) of the Schiff base li-
gand, respectively. The singlet signals at 164.56 and
20.21 ppm were due to azomethine carbon and methyl carbon
atoms of the ligand.[8,34] On the other hand, the spectrum of
the ligand showed peaks in the region of 146.06–119.34 ppm,
1
due to aromatic carbon atoms. H and 13C NMR bands of the
Schiff base ligand are depicted in Figure 1.
Figure 2. Photoluminescence spectra of the Schiff base ligand and its
metal complexes in DMF.
Figure 2 also shows the comparison of excitation and emis-
sion spectra of the ligand and its various complexes in the
solvent DMF. The complexes were used for the luminescent
measurements. The photoluminescence intensities and quan-
tum yields of metal complexes changed with respect to that of
the ligand upon complexation with various metal ions. As ob-
vious from Figure 2, the ligand exhibits an excitation maxi-
mum at 260 nm, which shifts to 258 nm upon binding to the
transition metal ions. Also, a decrease in excitation intensity
of the ligand was observed depending on complex formation
with the all transition metal ions. When excited at 260 nm, the
ligand showed an emission maximum at 402 nm, which also
shifted to 378 nm upon binding to the transition metal ions
(Figure 2). Thus, it is evident that the fluorescence emission
intensity of the ligand decreases dramatically depending on the
complex formation with the transition metal ions. This de-
crease of emission intensities is due to the formation of the
coordination complex of sulfur, oxygen, and nitrogen atoms
on compound ligand with the metal ions. These coordination
complexes make the energy transfer from the excited state of
the ligand to metal ions possible, thus increasing the non-radi-
ated transition of the ligand excited state and decreasing the
fluorescence emission. However, the degree of fluorescence
quenching increases upon complex formation with metal ions,
which have lower d-orbital electron number. The decrease in
1
Figure 1. Assignments of the H and 13C NMR signals in the ligand.
Since the solubility of the diamagnetic platinum(II) complex
in deutero solvents are not at the desired level, NMR spectro-
scopic data and the spectrum of this complex are not included
in the study.
Mass Spectrometry
The mass spectrum of the Schiff base ligand showed a mo-
lecular ion peak at m/z: 743.1 [M + H], which corresponds to
its proposed molecular formula. For CuII, NiII, CoII, MnII, PdII,
and PtII metal complexes, the following peaks were attribut-
able to the molecular ions; m/z: 918.3 [Cu + L + (CH3COO)
+ 3H2O]+, m/z: 880.8 [Ni + L + (CH3COO) + 2H2O + 3H],
m/z: 879.7 [Co + L + (CH3COO) + H2O + 2H], m/z: 796.2
[Mn + L]+, m/z:968.4 [Pd + L + 2CH3COO + H], m/z:1044.0
[Pt + L + 2Cl + 2H2O]+. The reference spectra of
[Mn(L)(AcO)]·5H2O and [Pt(HL)Cl2]·2H2O are shown in Fig-
ures S2a and S2b (Supporting Information).
Fluorescence Measurements
emission maxima was in the order of Cu2+ Ͻ Ni2+ Ͻ Co2+
Ͻ
The optical properties of the Schiff base ligand and its vari- Pd2+ Ͻ Pt2+ Ͻ Mn2+ for the complexes synthesized (Figure 2).
ous complexes were explored using UV/Vis and PL. Absorp- This clearly implicates an interaction between the metals and
Z. Anorg. Allg. Chem. 0000, 0–0
© 0000 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.zaac.wiley-vch.de
3

Job/Unit: Z13224
/KAP1
Date: 14-08-13 15:52:18
Pages: 9
M. Gulcan et al.
ARTICLE
Table 1. Photoluminescence data for Schiff base ligand and its metal complexes.
λmax Exa) /nm
In Exb)
749
λmax Emc) /nm
In Emd)
736
φfe) /%
τff) /ns
Ligand HL
260
402
42
3.94
(223; 242; 269)
(351;379;
433;473)
381
(355;400;
434;469)
399
[Cu(L)(AcO)]·4H2O
[Ni(L)(AcO)]·H2O
258
580
522
571
514
35
32
3.23
2.96
(222; 241; 270)
259
(221; 240; 270)
(352;378;
436;471)
[Co(L)(AcO)]·2H2O
[Pd(HL(AcO)2]·H2O
[Pt(HL)Cl2]·2H2O
[Mn(L)(AcO)]·5H2O
258
457
391
337
298
378
450
386
333
295
29
25
22
20
2.66
2.34
2.06
1.85
(222; 240; 268)
(354;401;
435;468)
405
(351;379;
433;470)
403
(350;378;
436;473)
404
(351;380;
435;476)
260
(221; 240; 271)
259
(222; 241; 270)
260
(222; 239; 270)
a) λmax Ex: maximum excitation wavelength. b) In Ex: maximum excitation intensity. c) λmaxEm: maximum emission wavelength. d) In Em:
maximum emission intensity. e) φf: quantum yield. f) τf: excited-state lifetime.
the ligand. The emission of the ligand being inhibited in this cence data for the ligand and its various complexes are summa-
case was dependent on the presence of a metal ion, and ligand rized in Table 1. The photoluminescent properties of these
photoluminescence in DMF is regarded as being dependent on compounds may indicate great potential for numerous optical
the d-block catalysts (metals) that are effective in DMF solu- and electronic applications.
tions. Quenching of fluorescence of the ligand by transition
metal ions during complexation is a rather common phenome-
non, which can be explained by processes such as magnetic
perturbation, redox-activity, electronic energy transfer,
etc.[35,36] Enhancement of fluorescence through complexation
Antimicrobial Activity
Antimicrobial activity of the newly prepared Schiff base li-
is, however, of much interest as it opens up the opportunity gand and its six metal complexes (CuII, NiII, CoII, MnII, PdII
for photochemical applications of these complexes.[37,38] It can and PtII) were screened for antibacterial activity against S. au-
be seen in Figure 2 that upon complexation of the ligand, the reus ATCC 6538, S. aureus ATCC 25923, B. cereus ATCC
photoluminescence intensities and quantum yields of metal 7064, M. luteus ATCC 9345 and E. coli ATCC 4230, and for
complexes decreased. This decrease in intensity is due to for- antifungal activity against C. albicans ATCC 14053, C. krusei
mation of complexation. Also, upon complexation of the li- ATCC 6258 and C. parapsilosis ATCC 22019 by using broth
gand, the maximum photoluminescence peak shifted from 402 microdilution procedure. Ampicillin trihydrate for bacteria and
to 378 nm, and other peaks and shoulder peaks become more fluconazole for yeast were used as standard agents. The antimi-
intense and obvious. Some electrons of atoms or moieties of crobial activities of the chemical compounds against tested mi-
this ligand have been affected by inserted metal ions. Maybe croorganisms are given in Table 2 and Table 3. According to
this emission wavelength difference can be used as tuning the results, all chemical compounds inhibited the growth of
properties in photoluminescent devices. The photolumines- bacterial strains with MIC values in the range of 40–
Table 2. The MICsa) of the ligand and its metal complexes against Gram-negative and Gram-positive bacterial strains.
B. cereus ATCC 7064 S. aureus ATCC
S. aureus ATCC
E. coli ATCC 4230 M. luteus ATCC
6538
25923
9345
Ligand (HL)
320
80
160
80
160
40
640
640
–
640
640
160
640
20
160
80
[Cu(L)(AcO)]·4H2O
[Ni(L)(AcO)]·H2O
[Co(L)(AcO)]·2H2O
[Mn(L)(AcO)]·5H2O
[Pd(HL(AcO)2]·H2O
[Pt(HL)Cl2]·2H2O
Ampicillin
320
320
320
160
320
5
640
320
320
160
320
5
640
160
320
160
320
10
320
160
320
160
320
10
a) The MICs values were determined as μg·mL–1 active compounds in medium.
4
www.zaac.wiley-vch.de
© 0000 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 0000, 0–0

Job/Unit: Z13224
/KAP1
Date: 14-08-13 15:52:18
Pages: 9
A Schiff Base Ligand and its Metal(II) Complexes
a)
Table 3. The MICs of the ligand and its metal complexes against cence intensities and quantum efficiencies. Upon complexation
fungal strains.
the luminescence peak shifted from 402 to 378 nm. These
compounds are interesting materials for applications in electro-
luminescent devices. The newly prepared Schiff base ligand
and its some metal complexes (CuII, NiII, CoII, MnII, PdII, and
PtII) were evaluated for in vitro the antimicrobial activities
towards bacterial and fungal tested strains. The results of the
study revealed that CuII complex have effective and selective
antibacterial and anti-yeast activity against tested microorga-
nisms with MIC values in the range of 40–80 μg·mL–1. Ad-
ditionally, the antifungal results showed that CoII and PtII com-
plexes have good anti-yeast activity against Candida species
(MICs, 80 μg·mL–1). Since multi-drug resistant microorga-
nisms pose a serious challenge to the medical community in
many countries around the world and there is an urgent
need to develop new agents.[42–44] Consequently, the
[Cu(L)(AcO)]·4H2O compound may be a new potential anti-
microbial substance against bacteria and fungi.
C. albicans
ATCC 14053 ATCC 22019
C. parapsilosis C. krusei
ATCC 6258
Ligand (HL)
160
160
80
160
80
[Cu(L)(AcO)]·4H2O 80
[Ni(L)(AcO)]·H2O
320
320
80
320
80
[Co(L)(AcO)]·2H2O 80
[Mn(L)(AcO)]·5H2O 320
[Pd(HL(AcO)2]·H2O 320
320
320
80
160
320
80
[Pt(HL)Cl2]·2H2O
Fluconazole
80
5
5
10
a) The MICs values were determined as μg·mL–1 active compounds in
medium.
640 μg·mL–1 as well as displayed antifungal activity with
MICs between 80–320 μg·mL–1.
The results of the antibacterial activity indicated that the
chemical compound named as [Cu(L)(AcO)]·4H2O showed
moderately antibacterial activity against whole tested bacterial
strains with MIC values in the range of 40–80 μg·mL–1, except
for E. coli ATCC 4230. On the contrary, the other chemical
compounds have poorly antibacterial activity against bacterial
strains with MICs between 160 and 640 μg·mL–1. The results
of this study revealed that E. coli ATCC 4230 (one Gram-
negative bacterium) were resistant against all tested chemical
substances (Table 2).
Table 3 presents the antifungal activities of the new synthe-
sized Schiff base ligand and its six metal complexes (CuII, NiII,
CoII, MnII, PdII and PtII) towards three yeast strains (C. al-
bicans ATCC 14053, C. krusei ATCC 6258 and C. parapsilosis
ATCC 22019). Our antifungal findings indicated that CuII,
CoII, and PtII complexes had good anti-yeast efficiency against
Candida species (MICs, 80 μg·mL–1). However, the ligand and
other three complexes exhibited weakly antifungal activity
with MIC values in the range of 160–320 μg·mL–1. Generally,
it suggested that the CuII complexes of several compounds
showed high antimicrobial activity than free ligands against
microorganisms.,[24,39–41] The findings obtained from this in-
vestigation were in agreement with the previous studies.
The results revealed that the chemical compound
[Cu(L)(AcO)]·4H2O possessed good antimicrobial efficiency
against both bacterial and fungal strains.
Experimental Section
General Procedure: All chemicals are commercially available and
were used without further purification. 9,10-Diphenylanthracene, di-
methylformamide (DMF), and methanol were purchased from Aldrich
Chem. Co. 1-Amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-thione (N-
aminopyrimidine-2-thione)[45] and 2,6-diformyl-4-methylphenol[46]
were synthesized according to the method described in literature.
The elemental analyses (C, H, N, S) were performed with a Leco
CHNS model 932 elemental analyzer. FT-IR spectra were obtained
using KBr pellets (4000–400 cm–1) with a Bio-Rad-Win-IR Spectro-
photometer. The electronic spectra in the range of 200–900 nm were
recorded in DMF with a Unicam UV2–100 UV/Vis spectrophotometer.
Magnetic measurements were carried out by Gouy method using
Hg[Co(SCN)4] as a calibrant. Molar conductance of the Schiff base
ligand and its transition metal complexes were determined in DMF at
room temperature with a IQ Scientific Instruments Multimeter. The 1H
NMR and 13C NMR spectra of the Schiff base were obtained with a
Bruker 300 MHz Ultrashield TM NMR instrument. LC/MS-API-ES
mass spectra were recorded with an Agilent model 1100 MSD mass
spectrophotometer. The single-photon fluorescence spectra of the
Schiff base ligand and its complexes were collected with a Perkin-
Elmer LS55 luminescence spectrometer. All the samples were prepared
in spectrophotometric grade DMF and analyzed in a 1 cm optical path
quartz cuvette. The concentration of the ligand and the complexes in
DMF was 1.0ϫ10–5 mol·L–1 and the samples were excited at 258 nm
wavelength. The quantum efficiencies of the ligand and the complexes
were calculated by using some standard materials like 9,10-diphenyl-
antracene.[47–49]
Conclusions
We report on the synthesis and spectroscopic study of the
new heterocyclic Schiff base ligand containing pyrimidine
rings and its metal complexes of the types [M(L)AcO]·nH2O,
[M(HL)(AcO)2]·nH2O and [M(HL)Cl2]·nH2O. Since the single
crystals of the complexes could not be isolated from any solu-
tions, no definitive structure can be described. But, the analyti-
cal, spectroscopic and magnetic data enable us to predict the
possible structures as shown in Figure 4. Moreover, investi-
gations of optical properties of the Schiff base ligand and its
various complexes in solution were performed. The ligand was
found to show an intense photoluminescence at 402 nm, and
Preparation of 2,6-Bis((E)-((5-benzoyl-2-thioxo-4-phenylpyrim-
idin-1(2H)-yl)imino)methyl)-4-(methyl)phenol (HL): The Schiff
base ligand (HL) was prepared by 2:1 condensation reaction between
N-aminopyrimidine-2-thione and 2,6-diformyl-4-methylphenol. A hot
ethanol solution (30 mL) of 2,6-diformyl-4-methylphenol (0.164 g,
1 mmol) and hot ethanol solution (30 mL) of N-aminopyrimidine-2-
the complexes showed a great change in maximum lumines- thione (0.614 g, 2 mmol) was mixed slowly with a constant stirring
Z. Anorg. Allg. Chem. 0000, 0–0
© 0000 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.zaac.wiley-vch.de
5

Job/Unit: Z13224
/KAP1
Date: 14-08-13 15:52:18
Pages: 9
M. Gulcan et al.
ARTICLE
0.133 g) in of methanol (15 mL) was added dropwise with continuous
stirring. The mixture was stirred at 60 °C for 1 h. The precipitated
compound was removed by filtration, washed with hot methanol and
dried in vacuo dessicator (Figure 4).
Preparation of [2,6-Bis((E)-((5-benzoyl-2-thioxo-4-phenylpyrim-
idin-1(2H)-yl)imino)methyl)-4-(methyl)phenolatoacetato]copper
Tetrahydrate ([Cu(L)(AcO)]·4H2O): Dark green solid; Yield 30%;
Mp: 219 °C. C45H40CuN6O9S2 (936,51 g·mol–1): calcd. C 57.71; H
4.31; N 8.97; S 6.85%; found C 57.46; H, 4.36; N, 8.94; S, 6.85%.
IR (KBr, selected data): ν˜
= 3450–3500 ν(OH/H2O), 3057
(C–Hpyrimidine), 1653 ν(C=O), 1576 (C=Nazomethine), 1340
ν(C–Ophenolic), 746,1230 ν(C=S), 559 (M–N), 420 (M–S). UV/Vis [λ
(nm), ε (m–1 cm–1)]: 516 (72), 462 (165), 364 (2370), 232 (3420);
μeff, 1.68 BM, Λo (S·cm2·mol–1) 12.1; API-ES: m/z: 918.3 [Cu + L
+ (CH3COO) + 3H2O]+.
Figure 3. Synthesis route of the Schiff base ligand (HL).
Preparation of [2,6-Bis((E)-((5-benzoyl-2-thioxo-4-phenylpyrim-
idin-1(2H)-yl)imino)methyl)-4-(methyl)phenolatoacetato]nickel
Monohydrate ([Ni(L)(AcO)]·H2O): Dark blue solid. Yield 45%; Mp:
190 °C (dec.). C45H34NiN6O6S2 (877,61 g·mol–1): calcd. C 61.59; H
3.90; N 9.58; S 7.31%; found C 61.41; H 3.81; N 10.04; S 7.76%. IR
(KBr, selected data): ν˜ = 3500–3550 ν(OH/H2O), 3056 (C–Hpyrimidine),
1653 ν(C=O), 1589 (C=Nazomethine), 1339 ν(C–Ophenolic), 745,1232
ν(C=S), 569 (M–N), 445 (M–S). UV/Vis [λ (nm), ε (m–1 cm–1)]:
620(39), 466(225), 412(1648), 234(2840); μeff, 2.51 BM, Λo
(S·cm2·mol–1) 4.54; API-ES: m/z: 880.8 [Ni + L + (CH3COO) + 2H2O
+ 3H].
(Figure 3). Afterwards the mixture was refluxed for 4 h. A yellow
precipitate was formed. The isolated solid precipitate was filtered off,
washed with hot ethanol and diethyl ether and dried in vacuo
over P2O5. Yellow, yield (50%), Mp 208 °C. C43H30N6O3S2
(742,87 g·mol–1): calcd. C 69.52; H 4.07; N 11.31; S 8.63%; found:
C 69.23; H 4.13; N 10.95; S 8.68%. IR (KBr, selected data): ν˜ = 3500
ν(OH/H2O), 3056 ν(C–Hpyrimidine), 2957 ν(CH3), 1659 ν(C=O), 1593
ν(C=Nazomethine) 1355 ν(C–Ophenolic), 739,1245 ν(C=S) cm–1. UV/Vis
[λ (nm)] 552,456,408,238,220. 1H NMR (300 MHz, CDCl3): δ = 11.76
(br. s, 1 H, OH), 9.25 (s, 2 H), 9.09 (s, 2 H), 7.92–7.90 (m, 4 H, ArH),
7.61 (t, J = 7.3 Hz, 2 H, ArH), 7.53–7.23 (m, 14 H, ArH), 2.39 (s, 3
H, CH3) ppm. 13C NMR (75 MHz, [D6]DMSO): δ = 191.9, 176.4,
165.9, 164.6, 146.1, 136.7, 136.5, 135.8, 134.8, 131.5, 130.4, 129.7,
129.4, 129.2, 128.9, 120.7, 119.3, 20.2 ppm. API-ES: m/z 743.1 [M +
H].
Preparation of [2,6-bis((E)-((5-benzoyl-2-thioxo-4-phenylpyrim-
idin-1(2H)-yl)imino)methyl)-4-(methyl)phenolatoacetato]cobalt
Dihydrate ([Co(L)(AcO)]·2H2O): Dark blue solid. Yield 45%; Mp:
190 °C (dec.). C45H36CoN6O7S2 (895,87 g·mol–1): calcd. C 60.33; H
4.05; N 9.38; S 7.16%; found C 59.47; H 3.99; N 9.31; S 6.86%. IR
General Preparation of the Metal Complexes: The ligand HL
(0.5 mmol, 0.372 g) was dissolved in a chloroform and methanol mix- (KBr, selected data): ν˜ = 3450 ν(OH/H2O), 3055 (C–Hpyrimidine), 1655
ture (50 mL; 1:1, v/v) and a solution of metal salts Cu(AcO)2·H2O ν(C=O), 1574 (C=Nazomethine), 1315 ν(C–Ophenolic), 742,1233 ν(C=S),
(0.5 mmol, 0.100 g),
Ni(AcO)2·4H2O
(0.5 mmol, 0.125 g),
540 (M–N), 431 (M–S). UV/Vis [λ (nm), ε (m–1 cm–1)]: 512(70),
Co(AcO)2·4H2O (0.5 mmol, 0.125 g), Mn(AcO)2·4H2O (0.5 mmol, 476(280), 452(1276), 230(2240); μeff, 2.62 BM, Λo (S·cm2·mol–1)
0.123 g), Pd(AcO)2 (0.5 mmol, 0.112 g), and PtCl2 (0.5 mmol,
5.93; API-ES: m/z: 879.7 [Co + L + (CH3COO) + H2O + 2H].
Figure 4. Suggested possible structures of the Schiff base metal complexes.
6
www.zaac.wiley-vch.de
© 0000 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 0000, 0–0

Job/Unit: Z13224
/KAP1
Date: 14-08-13 15:52:18
Pages: 9
A Schiff Base Ligand and its Metal(II) Complexes
Preparation of [2,6-Bis((E)-((5-benzoyl-2-thioxo-4-phenylpyrim- dilutions inoculated with each bacterium were incubated on a rotary
idin-1(2H)-yl)imino)methyl)-4-(methyl)phenolatoacetato]- shaker at 37 °C for 18 h at 150 rpm. The minimum inhibitory concen-
manganese Pentahydrate ([Mn(L)(AcO)]·5H2O): Brick red solid.
Yield 50%; Mp: 176 °C. C45H36CoN6O7S2 (945,92 g·mol–1): calcd. C
57.14; H 4.48; N 8.76; S 6.69%; found C 57.26; H 4.37; N 8.88; S
6.78%. IR (KBr, selected data): ν˜ = ~3450–3550 ν(OH/H2O), 3057
(C–Hpyrimidine), 1654 ν(C=O), 1574 (C=Nazomethine), 1335
ν(C–Ophenolic), 741,1233 ν(C=S), 545 (M–N), 442 (M–S). UV/Vis [λ
(nm), ε (m–1 cm–1)]: 528(47), 480(496), 464(1218), 232(3100); μeff,
5.82 BM, Λo (S·cm2·mol–1) 11.83. API-ES: m/z: 796.2 [Mn + L]+.
trations (MICs) of each chemical compounds were recorded as the
lowest concentration of each chemical compounds, comparing to nega-
tive controls (i.e. no turbidity).
Antifungal Assay: The antifungal activities of the compounds were
tested against 3 yeast (Candida albicans ATCC 14053, C. krusei ATCC
6258 and C. parapsilosis ATCC 22019) strains according to the guide-
lines in NCCLS approved standard document M27-A2, using the mic-
rodilution broth procedure.[51] Fluconazole was used as reference anti-
fungal agent. Solution of the test compounds and the reference drug
were dissolved in DMSO at a concentration of 2560 μg·mL–1. Two-
fold dilution of the compounds and the reference drug were prepared
to achieve the final concentrations (1280, 640, 320, 160, 80, 40, 20,
10, 5 Ͼ μg·mL–1). The last two tubes were selected as the positive
and the negative controls, respectively. While the negative control does
not inoculation with bacterial solution, the positive control was inocu-
lated with yeast suspension. Antifungal activities of the yeast strains
were performed in RPMI 1640 Medium (Sigma) buffered to pH 7.0
with 0.165 m morpholinopropanesulfonic acid (Sigma), as outlined in
document M27-A2. The stock yeast inoculum suspensions were ad-
justed to concentration of (1–2)ϫ103 cells·ml–1 by spectrophotometric
method and aliquot of 100 μL was added to each tube of the serial
dilution. The chemical compound-broth medium serial tube dilutions
inoculated with yeast were incubated on a rotary shaker at 37 °C for
18 h at 150 rpm. The minimum inhibitory concentrations (MICs) of
each chemical compounds were recorded as the lowest concentration
of each chemical compounds, comparing to negative controls (i.e. no
turbidity).
Preparation of [2,6-Bis((E)-((5-benzoyl-2-thioxo-4-phenylpyrim-
idin-1(2H)-yl)imino)methyl)-4-(methyl)phenoldiacetato]palladium
Monohydrate ([Pd(HL(AcO)2]·H2O): Dark brown solid. Yield 49%;
Mp: 215 °C. C47H38PdN6O8S2 (985,39 g·mol–1): calcd. C 57.29; H
3.89; N 8.53; S 6.51%; found C 56.98; H 3.87; N 8.62; S 6.61%. IR
(KBr, selected data): ν˜ = ~3400 ν(OH/H2O), 3056 (C–Hpyrimidine), 1653
ν(C=O), 1591 (C=Nazomethine), 1355 ν(C–Ophenolic), 743,1231 ν(C=S),
435 (M–S). UV/Vis [λ (nm), ε (m–1 cm–1)]: 532(42), 476(395),
1
402(1324), 234(2360). H NMR (300 MHz, CDCl3): δ = 11.68 (br. s,
1 H, OH), 9.26 (s, 2 H), 9.19 (s, 2 H), 7.90–7.88 (m, 4 H, ArH), 7.62
(t, J = 6.3 Hz, 2 H, ArH), 7.53–7.23 (m, 14 H, ArH), 2.37 (s, 3 H,
CH3), 2.07 (s, 6 H, CH3COO–) ppm. μeff, D; Λo (S·cm2·mol–1) 17.7.
API–ES: m/z: 968.4 [Pd + L + 2CH3COO + H].
Preparation of [2,6-bis((E)-((5-benzoyl-2-thioxo-4-phenylpyrim-
idin-1(2H)-yl)imino)methyl)-4-(methyl)phenoldichloride]platinum
Dihydrate ([Pt(HL)Cl2]·2H2O): Dark brown solid. Yield 48%; Mp:
210 °C (dec.). C47H38PdN6O8S2 (1044,89 g·mol–1): calcd. C 49.43; H
3.28; N 8.04; S 6.14%; found C 48.87; H 3.25; N 8.24; S 6.15%. IR
(KBr, selected data): ν˜ = 3500 ν(OH/H2O), 3055 (C–Hpyrimidine), 1659
ν(C=O), 1594 (C=Nazomethine), 1353 ν(C–Ophenolic), 752,1177 ν(C=S),
432 (M–S). UV/Vis [λ (nm), ε (m–1 cm–1)]: 508(86), 455 (290),
380(1480),232(2150); μeff, D; Λo (S·cm2·mol–1) 23.2. API-ES: m/z:
1044.0 [Pt + L + 2Cl + 2H2O]+.
Supporting Information (see footnote on the first page of this article):
1H(a) and 13C(b) NMR spectra of the Schiff base ligand. API-ES spec-
tra [Mn(L)(AcO)]·5H2O and [Pt(HL)Cl2]·2H2O complexes (a,b)
Biological Assay: Compounds: Test compounds were dissolved in Acknowledgements
DMSO (12.5%) with an initial concentration of 1280 μg·mL–1 and
then twofold serial dilutions of the compounds were prepared in cul-
ture medium.
The authors wish to thank TUBITAK (Project No: 104M367) and Pres-
idency of Scientific Research Projects of University of Yuzuncu Yil
(2011-FED-B009) for the financial support.
Cells: Bacterial strains were supplied from American Types Culture
Collection. Candida strains were obtained from Refik Saydam Hifsi-
sihha Research Institute, Ankara, Turkey.
References
Antibacterial Assay: The chemical compounds were evaluated for [1] C. Sousa, C. Freire, B. de Castro, Molecules 2003, 8, 894–900.
[2] A. L. El-Ansary, H. M. Abdel-Fattah, N. S. Abdel-Kader, Spec-
trochim. Acta A 2011, 79, 522–528.
[3] A. H. Kianfar, V. Sobhani, M. Dostani, M. Shamsipur, M. Roush-
ani, Inorg. Chim. Acta 2011, 365, 108–112.
their antibacterial activity against four Gram-positive (Staphylococcus
aureus ATCC 6538, S. aureus ATCC 25923, Bacillus cereus ATCC
7064 and Micrococcus luteus ATCC 9345) and one Gram-negative
(Escherichia coli ATCC 4230) bacteria as described by the guidelines
in NCCLS approved standard document M7-A6 using the microdilu-
tion broth procedure.[50] Ampicillin trihydrate was used as reference
antibacterial agent. Solutions of the compounds and the reference drug
were dissolved in DMSO at a concentration of 2560 μg·mL–1. The
twofold dilution of compounds and reference drug were prepared to
achieve the final concentrations (1280, 640, 320, 160, 80, 40, 20, 10,
5 Ͼ μg·mL–1). The last two tubes were selected as the positive and
the negative controls, respectively. While the negative control does not
inoculation with bacterial solution, the positive control was inoculated
with bacterial suspension. Antibacterial activities of the chemical com-
pounds were determined in Mueller-Hinton broth (Difco) medium at
pH 7.2 with an inoculum of (1–2)ϫ103 cells mL–1 by the spectropho-
tometric method and an aliquot of 100 μL was added to each tube
of serial dilution. The chemical compounds-broth medium serial tube
[4] M. Gülcan, M. Sönmez, Phosphorus Sulfur Silicon Relat. Elem.
2011, 186, 1962–1971.
˙
[5] M. Gülcan, M. Sönmez, I. Berber, Turk. J. Chem. 2012, 36, 189–
200.
[6] S. Broker, D. J. de Geest, G. S. Dunber, Inorg. Chim. Acta 1998,
282, 222–229.
[7] B. H. M. Mruthyunjayaswamy, O. B. Ijore, Y. Jadegoud, J. Braz.
Chem. Soc. 2005, 16, 783–789.
˙
[8] M. Sönmez, M. Çelebi, I. Berber, Eur. J. Med. Chem. 2010, 45,
1935–1940.
[9] F. Hueso-Urena, N. A. Illan-Cabeza, M. N. Moreno-Carreteroa,
J. M. Martinez-Martos, M. J. Ramirez-Exposito, J. Inorg. Bio-
chem. 2003, 94, 326–334.
[10] T. R. Chen, J. D. Chen, T. C. Keng, J. C. Wang, Tetrahedron Lett.
2001, 42, 7915–7917.
[11] L. Akcelrud, Prog. Polym. Sci. 2003, 28, 875–962.
Z. Anorg. Allg. Chem. 0000, 0–0
© 0000 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.zaac.wiley-vch.de
7

Job/Unit: Z13224
/KAP1
Date: 14-08-13 15:52:18
Pages: 9
M. Gulcan et al.
ARTICLE
[12] H. Wang, N. Song, H. Li, Y. Li, X. Li, Synth. Met. 2005, 151,
279–284.
[34] M. Tümer, N. Deligönül, A. Gölcü, E. Akgün, M. Dolaz, H. De-
mirelli, M. Dıg˘rak, Transition Met. Chem. 2006, 31, 1–12.
[35] A. W. Varnes, R. B. Dodson, E. L. Wehry, J. Am. Chem. Soc.
1972, 94, 946–950.
[13] M. Carrard, S. Goncalves-Conto, L. Si-Ahmed, D. Ades, A.
Siove, Thin Solid Films 1999, 352, 189–194.
[14] L. Feng, Z. Chen, Polymers 2005, 46, 3952–3956.
[15] Q. Fang, A. Tanimoto, T. Yamamoto, Synth. Met. 2005, 150, 73–
78.
[16] C. Qin, X. Wang, E. Wang, C. Hu, L. Xu, Inorg. Chim. Acta
2004, 12, 3683–3688.
[17] A. Heller, E. Wasserman, J. Chem. Phys. 1965, 42, 949–956.
[18] C. H. Chen, J. Shi, C. W. Tang, Macromol. Symp. 1998, 126-136,
1–48.
[19] M. Abkowitz, J. S. Facci, M. Stolka, Chem. Phys. 1993, 177,
783–792.
[36] J. A. Kemlo, T. M. Sheperd, Chem. Phys. Lett. 1977, 47, 158–
162.
[37] N. Chattopadhyay, A. Mallick, S. Sengupta, J. Photochem. Pho-
tobiol. A: Chem. 2006, 177, 55–60.
[38] P. Purkayastha, G. K. Patra, D. Datta, N. Chattopadhyay, Indian
J. Chem. A 2000, 39, 375–379.
[39] X. Y. Xu, J. Gao, M. Y. Wang, W. X. Ma, H. B. Song, K. P. Wain-
wright, J. Coord. Chem. 2005, 58, 669–676.
[40] A. A. Massoud, V. Langer, L. Öhrstrom, M. A. M. Abu-Youssef,
J. Coord. Chem. 2009, 62, 519–530.
[41] K. V. Sharma, V. Sharma, R. K. Dubey, U. N. Tripathi, J. Coord.
Chem. 2009, 62, 493–505.
[42] I. Berber, C. Cokmus, E. Atalan, Microbiology 2003, 72, 54–59.
[43] I. Berber, N. Alan, S. Ekin, H. Onlu, Asian J. Chem. 2010, 22,
3173–3185.
[44] I. Berber, S. Ekin, African J. Biotechnol. 2008, 7, 425–429.
[45] Y. Akçamur, B. Altural, E. Sarıpınar, G. Kollenz, O. Kappe, K.
Peters, E. Peters, H. J. Schering, Heterocycl. Chem. 1988, 25,
1419–1422.
[46] R. R. Gagne, C. L. Spiro, T. J. Smith, C. A. Hamann, W. R. Thies,
A. K. Shiemke, J. Am. Chem. Soc. 1981, 103, 4073–4081.
[47] Practical Fluorescence (Ed.: G. G. Guilbault), Marcel Dekker,
New York, 1990.
[48] A. Gilbert, J. Bagott, Essentials of Molecular Photochemistry,
CRC Press Boca Raton Inc, Florida, 1991.
[49] a) J. A. Osaheni, S. A. Jenekhe, J. Am. Chem. Soc. 1995, 117,
7389–7398; b) S. A. Jenekhe, J. A. Osaheni, J. Am. Chem. Mater.
1994, 6, 1906–1909.
[50] National Committee for Clinical Laboratory Standards, Methods
for dilution antimicrobial susceptibility tests for bacteria that
grow aerobically, Approved Standard M7-A6. NCCLS: Wayne,
PA, USA, 2003.
[51] National Committee for Clinical Laboratory Standards, Reference
method for broth dilution antifungal susceptibility testing of
yeasts, Approved Standard M27-A2. NCCLS: Wayne, PA, USA,
2002.
[20] L. Yang, X. H. Zhao, H. P. Zhou, Y. J. Wu, J. X. Yang, G. Q.
Shao, Y. P. Tian, Transition Met. Chem. 2005, 33, 31–437.
[21] M. Ozer, M. Kandaz, A. R. Ozkaya, M. Bulut, O. Guney, Dyes
Pigments 2008, 76, 125–132.
[22] W. L. Geary, Coord. Chem. Rev. 1971, 7, 81–122.
[23] J. N. Low, M. Quiros-Olozabal, J. M. Salas-Peregrin, F. Hueso-
Urena, M. N. Moreno-Carretero, Polyhedron 1996, 15, 3233–
3239.
˙
[24] M. Sönmez, M. Çelebi, A. Levent, I. Berber, Z. S¸entürk, J. Coord.
Chem. 2010, 63, 848–860.
[25] A. B. P. Lever, Inorganic Electronic Spectroscopy. 2nd ed, Elsev-
ier, Amsterdam, 1984.
˙
[26] M. Sönmez, M. Çelebi, A. Levent, I. Berber, Z. S¸entürk, J. Coord.
Chem. 2010, 63, 1986–2001.
[27] K. B. Gudasi, S. A. Patil, R. S. Vadavi, R. V. Shenoy, M. S. Patil,
J. Serb. Chem. Soc. 2006, 71, 529–542.
[28] A. A. Abdel Aziz, A. N. M. Salem, M. A. Sayed, M. M. Aboaly,
J. Mol. Struct. 2012, 1010, 130–138.
[29] L. J. Bellamy, The Infrared Spectra of the Complex Molecules,
2nd ed., Wiley Interscience, New York, 1970.
[30] K. Nakamoto, Infrared Spectra and Raman Spectra of Inorganic
and Coordination Compounds, John Wiley & Sons, New York,
1997.
[31] Z. Önal, B. Altural, Turk. J. Chem. 1999, 23, 401–405.
[32] T. M. A. Ismail, A. A. Saleh, M. A. E. Ghamry, Spectrochim. Acta
A 2012, 86, 276–288.
[33] A. A. A. Abou-Hussein, W. Linert, Spectrochim. Acta A 2012, 95,
596–609.
Received: May 1, 2013
Published Online: ᭿
8
www.zaac.wiley-vch.de
© 0000 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 0000, 0–0

Job/Unit: Z13224
/KAP1
Date: 14-08-13 15:52:18
Pages: 9
A Schiff Base Ligand and its Metal(II) Complexes
M. Gulcan,* H. Zengin, M. Çelebi, M. Sönmez,
˙
I. Berber ............................................................................ 1–9
2,6-Bis((E)-((5-benzoyl-2-thioxo-4-phenylpyrimidin-1(2H)-yl)-
imino)methyl)-4-(methyl)phenol and its Metal(II) Complexes:
Synthesis, Spectroscopy, Biological Activity, and Photolumin-
escence Features
Z. Anorg. Allg. Chem. 0000, 0–0
© 0000 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.zaac.wiley-vch.de
9