Synthesis, spectroscopic, and cyclic voltammetric studies of ferrocene containing vic-dioxime ligand and its complexes with Ni(II), Cu(II), Co(II), Cd(II) and Zn(II)

Article abstract of DOI:10.1016/j.ica.2013.06.012

A vic-dioxime ligand containing the ferrocene group anti-β- ferrocenylethylamino p-chlorophenylglyoxime (1) was synthesized from the reaction of β-ferrocenylethylamine with anti-chloro-p-chloro- phenylglyoxime. The mononuclear Ni(II), Cu(II), Co(II), Zn(II), and Cd(II) complexes of the vic-dioxime ligand were prepared and characterized using elemental analyses, mass spectra, fourier transform infrared spectroscopy (FT-IR), UV-Vis spectroscopy (UV-Vis), Magnetic susceptibility, nuclear magnetic resonance spectroscopy (¹H NMR, and ¹³C NMR) techniques. The redox behavior was studied using cyclic voltammetry and revealed metal-centered reduction processes for all complexes.

Full text of DOI:10.1016/j.ica.2013.06.012

Inorganica Chimica Acta 405 (2013) 326–330
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Inorganica Chimica Acta
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Synthesis, spectroscopic, and cyclic voltammetric studies of ferrocene
containing vic-dioxime ligand and its complexes with Ni(II), Cu(II), Co(II),
Cd(II) and Zn(II)
⇑
Pervin Deveci , Bilge Taner
Department of Chemistry, Selcuk University, Faculty of Science, Konya, Turkey
a r t i c l e i n f o
a b s t r a c t
Article history:
A vic-dioxime ligand containing the ferrocene group anti-b-ferrocenylethylamino p-chlorophenylglyoxime
(1) was synthesized from the reaction of b-ferrocenylethylamine with anti-chloro-p-chloro-
phenylglyoxime. The mononuclear Ni(II), Cu(II), Co(II), Zn(II), and Cd(II) complexes of the vic-dioxime
ligand were prepared and characterized using elemental analyses, mass spectra, Fourier transform infrared
spectroscopy (FT-IR), UV–Vis spectroscopy (UV–Vis), magnetic susceptibility, nuclear magnetic resonance
spectroscopy (1H NMR, and 13C NMR) techniques. The redox behavior was studied using cyclic voltamme-
try and revealed metal-centered reduction processes for all complexes.
Received 19 February 2013
Received in revised form 31 May 2013
Accepted 7 June 2013
Available online 14 June 2013
Keywords:
vic-Dioxime
Ferrocene
Ó 2013 Elsevier B.V. All rights reserved.
b-Ferrocenylethylamine
Metal complex
1. Introduction
knowledge, this is the first manuscript which includes the synthesis,
characterization and electrochemical properties of this vic-dioxime
The coordination chemistry of vic-dioxime compounds has be-
come of topic of increasing interest and has also been studied from
a variety of perspectives by many different research groups [1–4].
These compounds have been employed in various fields, including
extraction [5], optical materials [6], bioorganic systems [7], and
medicine [8,9]. Like vic-dioxime compounds, ferrocene derivatives
have attracted the interest of many scientists and research groups
worldwide due to their numerous applications in various fields of
science, ranging from biology to materials chemistry [10,11]. The
numerous applications of ferrocene derivatives in such fields as
non-linear optical materials [12], electrochemical sensors [13], li-
quid crystals [14], catalysis [15], and nanoparticles [16] have con-
tributed to the increased interest in their chemistry. In addition,
the introduction of groups with coordinating capabilities further
allows the ferrocenyl moiety to become an organometallic ligand
that can bind with other metal centers, thereby enhancing their
properties [17,18]. Hence, ferrocene-containing ligands have at-
tracted growing attention in coordination chemistry due to their
well-behaved redox activity and their unique coordination proper-
ties [19–22]. These findings prompted us to synthesize a new vic-
dioxime ligand and the associated Ni(II), Cu(II), Co(II), Cd(II), and
Zn(II) complexes by incorporating ferrocene moieties; moreover,
we studied the electrochemical redox behavior of these new types
of compounds with the parent ferrocene. To the best of our
ligand and its Ni(II), Cu(II), Co(II), Cd(II) and Zn(II) complexes.
2. Experimental
2.1. Materials and measurements
b-Ferrocenylethylamine [23–25] and anti-chloro-p-chloro-
phenylglyoxime [26,27] were prepared according to the procedures
reported in the literature. All other chemicals were purchased from
Merck or Sigma–Aldrich and used as supplied. Silica gel (70–230
mesh) was used as the stationary phase in all chromatographic sep-
aration processes. All organic solvents were dried and purified via
the typical methods. All the processes performed in aqueous media
and the preparation of the aqueous solutions were carried out using
ultra-pure water with a resistance of ꢀ18.3 M
X cm (Human Power
1+ Scholar purification system). Elemental analyses (i.e., for C, H, and
N) were performed using a LECO-932 CHNSO model analyzer. Nucle-
ar magnetic resonance (NMR) experiments were performed in a Var-
ian Unity INOVA 500 spectrometer using a 5 mm ID-PFG probe at
298.15 K. Moreover, samples were dissolved in dimethyl sulfoxide
(DMSO). Chemical shifts were reported in ppm relative to the tetra-
methylsilane (TMS) standard for proton (1H) and carbon-13 (13C)
NMR spectra. The infrared (IR) spectra of the solid samples were re-
corded on a Perkin-Elmer Spectrum 100 Fourier transform infrared
(FT-IR) spectrometer (Universal/ATR Sampling Accessory). The
UV–Vis spectra were obtained on Shimadzu UV–1700 visible
⇑
Corresponding author. Tel.: +90 332 2233892; fax: +90 332 2412499.
E-mail address: pervindeveci@gmail.com (P. Deveci).
0020-1693/$ - see front matter Ó 2013 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.ica.2013.06.012

P. Deveci, B. Taner / Inorganica Chimica Acta 405 (2013) 326–330
327
recording spectrophotometers. Magnetic moments of the com-
2.4. Synthesis of the vic-dioxime complexes: 5, 6
plexes were measured using a Sherwood Scientific Model MX1 Gouy
magnetic susceptibility balance at room temperature with
Hg[Co(SCN)4] as the calibrate; diamagnetic corrections were calcu-
lated from Pascal’s constants. The melting points were determined
using an electrothermal apparatus and were uncorrected. The mass
spectra (MS) were recorded on a Bruker Micro TOF LC–MS spectrom-
eter. All the electrochemical experiments were performed using a
CH Instruments electrochemical analyzer (model 600C series)
equipped with a BAS C3 cell stand. The working electrode was a bare,
glassy carbon disk (BAS Model MF-2012) with a geometric area of
0.027 cm2. The reference electrode was Ag/Ag+ (0.01 M) in nonaque-
ous media, and the counter electrode was a Pt wire.
A solution of CdCl2Á6H2O (0.114 g, 0.5 mmol) or ZnCl2 (0.07 g
0.5 mmol) in water (5 mL) was added to a solution of 1 (0.22 g,
0.5 mmol) in 5 mL of ethanol at room temperature. While stirring
at room temperature, NaOH (1%) was added to increase the pH
to 8. The reaction mixture was stirred for 30 min at room temper-
ature, and 2 mL of water was then added to this solution. The pre-
cipitate was filtered off, washed several times with water, and then
dried in a vacuum.
5: Yield: 0.14 g (46%). Mp: 219 °C. Color: Yellow. Anal. Calc. for
C
20H21Cl2N3O3FeCd: C, 40.61; H, 3.58; N, 7.11. Found: C, 40.57; H,
3.56; N, 7.15%. MS: m/z 590.955 (M)+(Calc. 590.934). FT-IR (mmax
cmÀ1): 3190, 3095, 2980, 1620, 1475, 966 cmÀ1 1H NMR (DMSO-
/
.
2.2. Synthesis of the anti-b-ferrocenylethylamino p-
chlorophenylglyoxime (1)
d6), d (ppm): 2.45 (t, 2H, CH2), 3.05–3.22 (m, 2H, CH2), 4.01 (t,
2H, C5H4), 4.03 (t, 2H, C5H4), 4.07 (s, 5H, C5H5), 7.52 (dd, 2H,
ArH), 7.58 (dd, 2H, ArH), 5.80 (t, 1H, NH), 10.13 (s, 1H, OH). 13C
NMR (DMSO-d6), d (ppm): 32.24, 40.23, 64.42, 66.24, 68.35,
85.28, 125.35, 126.23, 129.32, 130.43, 148.72, 149.35.
A
solution of anti-chloro-p-chlorophenylglyoxime (0.70 g,
3 mmol) and triethylamine (0.42 mL, 3 mmol) in ethanol (15 mL)
was added to a stirred mixture of b-ferrocenylethylamine (0.68 g,
3 mmol) in 15 mL of methanol. The mixture was stirred at room
temperature for 2 h and monitored by thin layer chromatography
(TLC) using ethyl acetate/n-hexane (2:1). The solvent was evapo-
rated, and the residue was purified via column chromatography
with silica gel as the stationary phase and ethyl acetate/n-hexane
(2:1) as the mobile phase, thereby producing the vic-dioxime
derivative 1.
6: Yield: 0.14 g (50%). Mp: >350 °C. Color: Yellow. Anal. Calc. for
C
20H21Cl2N3O3FeZn: C, 44.37; H, 3.91; N, 7.77. Found: C, 44.43; H,
3.95; N, 7.70%. MS: m/z 541.867 (MH)+ (Calc. 541.968) FT-IR (mmax
cmÀ1): 3195, 3090, 2975, 1627, 1475, 966 cmÀ1 1H NMR (DMSO-
/
.
d6), d (ppm): 2.43 (t, 2H, CH2), 3.05–3.19 (m, 2H, CH2), 4.00 (t,
2H, C5H4), 4.01 (t, 2H, C5H4), 4.08 (s, 5H, C5H5), 7.50 (dd, 2H,
ArH), 7.61 (dd, 2H, ArH), 5.83 (t, 1H, NH), 10.15 (s, 1H, OH). 13C
NMR (DMSO-d6), d (ppm): 31.28, 40.44, 63.27, 64.33, 67.23,
85.89, 125.51, 126.45, 128.31, 135.42, 147.15, 150.26.
Yield: 0.77 g (60%). Mp: 140 °C. Color: Yellow. Anal. Calc. for C20-
H20ClN3O2Fe: C, 56.46; H, 4.74; N, 9.88. Found: C, 56.54; H, 4.79; N,
10.06%. MS: m/z 426.102 (MH)+ (Calc. 426.066) FT-IR ( max/cmÀ1):
m
2.5. Electrochemical studies
3340, 3190, 3095, 2980, 1640, 1455, 970. 1H NMR (DMSO-d6), d
(ppm): 2.48 (t, 2H, CH2), 3.05–3.19 (m, 2H, CH2), 3.96 (t, 2H,
C5H4), 4.00 (t, 2H, C5H4), 4.03 (s, 5H, C5H5), 7.50 (dd, 2H, ArH),
7.60 (dd, 2H, ArH), 5.80 (t, 1H, NH), 9.77 (s, 1H, OH), 11.87 (s,
1H, OH). 13C NMR (DMSO-d6), d (ppm): 30.28, 41.64, 65.75,
68.42, 68.98, 85.80, 126.25, 128.93, 129.55, 131.34, 145.77, 148.29.
The glassy carbon electrodes were prepared by first polishing
them first with fine, wet emery papers (grain size 4000) (Buehler,
Lake Bluff, IL, USA) and then 0.1 and 0.05
polishing pads (Buehler, Lake Bluff, IL, USA) in order to give them
mirror-like appearance. The electrodes were sonicated for
lm alumina slurry on
a
5 min in water and in a 50:50 (v/v) isopropyl alcohol and acetoni-
trile (IPA + MeCN) solution purified over activated carbon. Prior to
the electrochemical experiments, the electrodes were dried with
an argon gas stream, and the solutions were purged with pure ar-
gon gas (i.e., 99.999%) for at least 10 min; additionally, an argon
atmosphere was maintained over the solution during the experi-
ments. Electrochemical studies of the compounds were performed
in a solution of 1 mM 1 and its complexes in 0.1 M tetrabutylam-
monium tetra fluoro borate (TBATFB) in DMSO; moreover, an Ag/
Ag+ (0.01 M) reference electrode using cyclic voltammetry (CV)
with a scan rate of 200 mV sÀ1 between 1 and À2.5 V was used.
2.3. Synthesis of the vic–dioxime complexes: 2–4
A solution of NiCl2Á6H2O (0.059 g, 0.25 mmol), CuCl2Á2H2O
0.25 mmol) and CoCl2Á6H2O (0.059 g, 0.25 mmol) in water (5 mL)
was added to a solution of 1 (0.22 g, 0.5 mmol) in 5 mL of ethanol
at room temperature. A distinct change in color and a decrease in
the pH of the solution (3.5–4.0) were observed. While stirring at
room temperature, NaOH (1%) was added to increase the pH to 7.
The reaction mixture was stirred for 30 min at room temperature,
and 2 mL water was then added to this solution. The resulting pre-
cipitate was filtered off, washed several times with water, and then
dried in a vacuum.
3. Results and discussion
2: Yield: 0.17 g (75%). Mp: 284 °C. Color: Dark reddish. Anal.
Calc. for C40H38Cl2N6O4Fe2Ni: C, 52.98; H, 4.23; N, 9.27. Found: C,
52.96; H, 4.28; N, 9.22%. MS: m/z 907.354 (MH)+, (Calc. 907.045).
The new redox active vic-dioxime ligand (1) was synthesized
from the condensation reaction of anti-chloro-p-chloro-
phenylglyoxime [23–25] and b-ferrocenylethylamine [26,27]
(Scheme 1). The ligand was characterized by elemental analysis
and FT-IR, UV–V, 1H NMR, and 13C NMR spectroscopy.
The Ni(II), Cu(II), Co(II), Cd(II), and Zn(II) complexes were pre-
pared by the reaction of the ligand (1) in a 2:1 or 1:1 (metal:ligand)
molar ratio with metal chlorides. The spectroscopic analyses for
the complexes indicated a 1:2 stoichiometry for Ni(II), Cu(II), and
Co(II) complexes and a 1:1 stoichiometry for Cd(II) and Zn(II) com-
plexes (Scheme 1).
FT-IR (m
max/cmÀ1): 3180, 3070, 2990, 1770, 1630, 1518, 960. 1H
NMR (DMSO-d6), d (ppm): 2.49 (t, 4H, CH2), 3.05–3.19 (m, 4H,
CH2), 4.00 (t, 4H, C5H4), 4.03 (t, 4H, C5H4), 4.05 (s, 10H, C5H5),
7.50 (dd, 4H, ArH), 7.60 (dd, 4H, ArH), 5.82 (t, 2H, NH), 14.54 (s,
2H, OH). 13C NMR (DMSO-d6), d (ppm): 31.24, 41.56, 65.34,
67.52, 68.26, 84.30, 125.21, 127.43, 128.24, 130.44, 146.33, 149.35.
3: Yield: 0.14 g (60%). Mp: 166 °C. Color: Dark green. Anal. Calc.
for C40H38Cl2N6O4Fe2Cu: C, 52.69; H, 4.20; N, 9.22. Found: C, 52.60;
H, 4.25; N 9.26%. MS: m/z 912.122 (MH)+ (Calc. 912.040). FT-IR
(m .
max/cmÀ1): 3186, 3095, 2980, 1775, 1632, 1480, 965 (N–O) cmÀ1
4: Yield: 0.16 g (68%). Mp: >350 °C. Color: Brown. Anal. Calc. for
3.1. FT-IR analysis
C
40H42Cl2N6O6Fe2Co: C, 50.89; H, 4.49; N, 8.91. Found: C, 50.85; H,
4.42; N, 8.97%. MS: m/z 944.213 (MH)+ (Calc. 944.065. FT-IR (mmax
/
The positions of the relevant IR bands were presented in the
experimental section. The formation of the ligands was confirmed
cmÀ1): 3195, 3090, 2985, 1780, 1618, 1480, 960 cmÀ1
.

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P. Deveci, B. Taner / Inorganica Chimica Acta 405 (2013) 326–330
Scheme 1. Structures of 1–6.
by the appearance of high intensity absorption bands due to m(C@N)
stretching vibrations at approximately 1640 cmÀ1 and the m(N–O)
vibrations at approximately 970 cmÀ1 [28]. The broad absorption
bands at 3340 and 3190 cmÀ1 were assigned to the m(N–H) and
m(O–H) stretching vibrations of the vic-dioxime ligands. In the FT-
IR spectra of the complexes, m(C@N) stretching vibrations were
shifted approximately 10–22 cmÀ1 to lower wave numbers. This
indicates that the azomethine nitrogen is bonded to metallic ions
[29]. The oxime hydroxyl stretching of the free ligand was absent,
while new vibrational bands of an intermolecular hydrogen bond
from the ferrocenyl and vic-dioxime groups were clearly observed.
In the 1H NMR spectra of ligand 1, a broad signal from the aromatic
primary amine group disappeared, and a new chemical shift at
about 5.80 ppm was observed as a triplet, which could be assigned
to the –NH proton. In all cases, the ferrocenyl moieties gave rise to
expected patterns where the unsubstituted C5H5 ring shows up as a
strong singlet at about 4.03 ppm and the monosubstituted C5H4
ring gives two triplets in the range 4.00–3.96 ppm [34]. The aro-
matic ring protons were observed at about 7.60 and 7.50 ppm as
two doublets of doublets. The chemical shifts from the N–OH pro-
tons were observed at 11.87 and 9.77 ppm as singlets for the ligand.
These two deuterium exchangeable singlets correspond to two
nonequivalent –OH protons, which also indicate the anti-configura-
tion of the –OH groups relative to one another (Fig. 1) [35]. In the 1H
NMR spectra of 2, the chemical shifts belonging to the –OH protons
in the vic-dioxime ligand (1) disappeared after complexation with
the Ni(II) ion, and the presence of a new resonance at a lower field
of 14.54 ppm could be attributed to the formation of the hydrogen
bridge, which could easily be identified via the deuterium exchange
[36]. In the 1H NMR spectra of 5 and 6, the peaks corresponding to
m
(O–HÁ Á ÁO) between the two oxime groups were observed in the
region of 1770–1780 cmÀ1 for the complexes 2–4 [30].
3.2. UV–Vis spectroscopy and magnetic susceptibility
The electronic transitions of all the compounds in DMSO (10À4
M) at 200–600 nm were recorded. The band at about 265 nm can
be attributed to
p–
p⁄ transitions [31]. The band or shoulder at
about 330 nm for all compounds could be characterized as n–p⁄
transitions [32]. The weak absorption bands between 450 and
470 nm that can be assigned to ferrocenyl metal-to-ligand charge
transfer bands. The spectra of complex 2 exhibit less intense
absorption bands in the range of 375–480 nm. This band could
be attributed to the d-d transitions of square planar Ni(II) com-
plexes. The weak d–d transition of complexes copper and cobalt
were not observed. Also, the d–d bands should be present at low
intensities in this range, but they are masked by the stronger CT
absorption band [33]. The magnetic susceptibility values of the
complexes show that the Ni(II), Cd(II) and Zn(II) complexes are dia-
magnetic, while the Cu(II) and Co(II) complexes are paramagnetic.
The measured values for the Cu(II) and Co(II) complexes are 1.73
B.M. and 3.85 B.M. respectively, which corresponds to a single elec-
tron. These values also show that the Ni(II) and Cu(II) complexes
are of square-planar structure and that the Co(II) complexes are
of octahedral structure. (Scheme 1).
N–OH were observed at 10.13 and 10.15 ppm, respectively. The 13
C
NMR spectrum is one of the most convenient ways to determine the
structure of vic-dioximes. The 13C NMR spectra of the ligand shows
signals that are typical of a monosubstituted ferrocene moiety in
the range of 67.35–85.80 ppm, which agrees with previous results
reported in the literature [37,38]. In the 13C NMR spectra of 1, the
signals at 145.77 and 148.29 ppm were assigned to the carbon
atoms of the vic-dioxime group. Two frequencies of the dioxime
group in the 13C NMR spectra indicate that the vic-dioxime has an
anti-structure [36,39]. The 13CNMR spectra of the complexes are
similar to those of the corresponding vic-dioxime. Upon complexa-
tion with the Ni(II), Cd(II), and Zn(II) cations, the free ligand
resonances shifted slightly as expected.
3.4. Electrochemical studies
3.3. NMR spectra
The cyclic voltammograms of the vic-dioxime ligands and the
associated complexes were obtained in DMSO (0.1 M TBATFB) at
the glassy carbon (GC) electrode to investigate the electrochemical
The structure of ligand 1 and complexes 2, 5, and 6 were evident
from the 1H NMR spectral pattern, and the proton signals stemming

P. Deveci, B. Taner / Inorganica Chimica Acta 405 (2013) 326–330
329
Fig. 1. 1H NMR spectrum of the 1.
Fig. 2. Cyclic voltammograms recorded for the oxidation of 1.0 mM 4 at a GC
electrode in DMSO containing 0.1 M TBATFB with the potential range of 0–1 V with
different scan rates.
behaviors and the effects of the structural differences on the elec-
tron transfer kinetics of the pendant ferrocene (Fc) group. The vol-
tammograms were recorded at 200 mV sÀ1 from 0 V to +1 V versus
Ag/Ag+ (0.01 M) and demonstrated a well-defined pair of symmet-
ric peaks, the anodic peak, and the corresponding cathodic peak lo-
cated around +0.5 V, all of which stem from the redox active
ferrocenyl substituents (Table 1, Fig. 2).
was used as the solvent, and TBATFB served as the supporting elec-
trolyte at a scan rate of 200 mV sÀ1. The CV curves for 1–3 and 6 are
shown in Fig. 3.
All of the compounds exhibit a quasireversible process (about
E1/2 = 0.50 V) attributable to the ferrocene couple. The CV of 1 and
3 exhibit an irreversible reduction at À1.96 and À1.63 V, respec-
tively, assigned to the imine moiety [43]. Complexes 2–4 show an-
other redox wave, which is attributed to the different redox states
of the metal ions. For 2, an irreversible process where Epc: À1.25 V
was attributed to the Ni(II)/Ni(I) couple [44]. For 3, the irreversible
wave at Epc: 0.10 V corresponds to the Cu(II)/Cu(I) couple [45]. For
the Co(II) complex, the reduction peak corresponding to Co(II)/
Co(I) at Epc = À1.25 V was observed [46]. For the Ni(II) and Co(II)
complexes, the absence of the reduction peak of the imino group
indicates that the reduction potentials of the dianionic ligands have
been shifted beyond the lower limit of the potential interval
considered in the experimental measurements due to the lack of
All of the compounds were displayed in ways that are typical for
the one-electron reversible oxidation of ferrocenes at almost iden-
tical potential values, which is attributed to the Fe2+/Fe3+ transfor-
mation. The peak potentials and peak currents were not
significantly influenced by the structural changes in the vic-diox-
ime derivatives. This means that the ferrocene redox centers are
well isolated from the vic-dioxime moieties [40]. At the same time,
the formal potential of Ni(II), Cu(II), Co(II), Cd(II), and Zn(II) metal
complexes were quite close, thereby indicating that these metallic
ion groups have a similar electronic effect on the iron center and
that all ferrocene subunits are in nearly equivalent environments
[41].
The separation of the anodic and the cathodic peak potentials,
D
Ep, were 77, 91, 113, 108, 115, 87, and 84 mV at 200 mV sÀ1 for
Fc and 1–6, respectively. These values are larger than that expected
for a reversible electron transfer reaction, which is given by 59/n
mV where n is the number of electrons transferred in the process.
At higher scan rates,
was observed ( Ep P 145 mV) possibly due to the onset of kinetic
m(m DEp
P 800 mV sÀ1, Fig. 2) broadening of
D
complications [42]. No splitting was observed for the ferrocene
couple, i.e., even at a scan rate of 25 mV sÀ1, showing that the
two ferrocenyl moieties behave independently and are oxidized
at the same potential in all compounds. The reduction properties
of ligand 1 and its metal complexes 2–6 were studied via CV under
nitrogen in the potential range of 1.0 to À2.5 V. A DMSO solution
Table 1
Cyclic voltammetric data in millivolts of Fc, 1–6 recorded on a GC working electrode,
platinum-wire auxiliary electrode and Ag/AgCl reference electrode in DMSO at
ambient temperature, scan rate 200 mV using TBATFB.
a
b
Compound
Epa (mV)
Epc (mV)
E1/2 or Ep (mV)
DEp (mV)
Fc
1
2
3
4
521
524
543
507
555
530
523
444
433
430
399
440
443
439
483
479
487
453
498
487
481
77
91
113
108
115
87
Fig. 3. Cyclic voltammograms recorded for the reduction of 1.0 mM 1 (black curve),
2 (green curve), 3 (blue curve), 6 (red curve), at a GC electrode in DMSO containing
0.1 M TBATFB with the potential range of 1 to À2.5 V with a scan rate of 200 mVÀ1
.
5
6
(For interpretation of the references to color in this figure legend, the reader is
referred to the web version of this article.)
84

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P. Deveci, B. Taner / Inorganica Chimica Acta 405 (2013) 326–330
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transferable hydroxylic protons [47]. The Cd(II) and Zn (II) com-
plexes show a CV voltammogram in line with expectations.
Therefore, only the voltammogram for the Zn(II) complexes is
shown in Fig. 3. Additionally, oxime group reductions in these com-
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4. Conclusion
ˇ
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phenylglyoxime (1) was prepared from the reaction of b-Ferroce-
nylethylamine with anti-chloro-p-chlorophenyglyoxime and
employed as a bidentate ligand for the formation of relatively sta-
ble Ni(II), Cu(II), Co(II), Cd(II), and Zn(II) complexes. Although these
complexes have the ferrocenyl group linked to the metal centers,
the electrochemical study shows no electronic communication be-
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Acknowledgement
We thank the Research Foundation of The Selcuk University
(BAP) for financial support of this work.
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