Synthesis and characterization of new vic-dioximes and their metal complexes with Cu(II), Ni(II), and Co(II) salts

Article abstract of DOI:10.1134/S1070328407030050

4-Acetyldiphenyl sulfide and 4,4-diacetyldiphenyl sulfide were synthesized from diphenyl sulfide and acetyl chloride in the presence of AlCl₃ as catalyst in the Friedel-Crafts reaction. Subsequently, the ketooxime and glyoxime derivatives were

Full text of DOI:10.1134/S1070328407030050

ISSN 1070-3284, Russian Journal of Coordination Chemistry, 2007, Vol. 33, No. 3, pp. 184–189. © Pleiades Publishing, Ltd., 2007.
Synthesis and Characterization of New vic-Dioximes
and Their Metal Complexes with Cu(II), Ni(II), and Co(II) Salts1
A. Cos¸kuna and Z. E. Koçb
a Department of Chemistry, Faculty of Education, Selcuk University, Konya, Turkey
b Department of Chemistry, Faculty of Arts and Sciences, Selcuk University, Konya, Turkey
e-mail: acoskun42@selcuk.edu.tr
Received March 23, 2006
Abstract—4-Acetyldiphenyl sulfide and 4,4'-diacetyldiphenyl sulfide were synthesized from diphenyl sulfide
and acetyl chloride in the presence of AlCl3 as catalyst in the Friedel–Crafts reaction. Subsequently, the
ketooxime and glyoxime derivatives were also prepared. The metal complexes of the glyoximes, such as copper,
nickel, and cobalt complexes were prepared. The BF2+ capped Ni(II) mononuclear complex of 4-thiophenox-
1
yphenylglyoxime was prepared. The structures of these ligands were identified by FT-IR, H NMR, and 13C
NMR spectral data and elemental analysis. The structures of the complexes were identified by FT-IR, elemental
analysis, and magnetic measurements.
DOI: 10.1134/S1070328407030050
1
INTRODUCTION
bis(dioxime) system were replaced by the BF2 group,
has been widely investigated [13]. This substitution has
also enhanced markedly the stability of the dioxygen
adduct by removing the labile acidic protons from the
vicinal dioxime ligands [14].
Numerous vicinal dioximes (vic-dioxime) and
their transition metal complexes have been investi-
gated [1]. The exceptional stability and unique elec-
tronic properties of these complexes can be attrib-
uted to their planar structure which is stabilized by
hydrogen bonding [2]. The high stability of the com-
plexes with vic-dioxime ligands has been used exten-
In the present paper, we describe the synthesis and
characterization of two new ketooximes—4-isonitro-
soacetyldiphenyl sulfide (HL) and 4,4'-diisonitrosoacetyl-
sively for various purposes. Oximes are used as addi- diphenyl sulphide (H2L), two new glyoximes—4-
tive materials for the improvement of pigments,
mechanic oils, epoxy resins and rubber, in industry,
etc. [3]. Recently, some oximes and their alkyl, oxy-
alkyl, and amino derivatives were proved to have
physiological and biological activity [4–6]. vic-
Dioximes also have received considerable attention
as model compounds which mimic biofunctions,
such as reduction of vitamin B12 [7, 8]. The presence
of moderately acidic hydroxy groups and slightly
basic nitrogen atoms makes vic-dioxime amphoteric
ligands that form square-planar, square-pyramidal,
or octahedral complexes with transition metal ions,
such as Cu(II), Ni(II) and Co(II), as central atoms
[7, 9–11].
The dioxygen binding ability of the bis(dioxi-
mate)cobalt(II) complexes has been the focus of con-
siderable attention in recent years and has been exten-
sively involved in the design, synthesis, and character-
ization of several classes of compounds that have been
shown to reversibly bind dioxygen [12]. In addition, a
group of macrocylic (E, E)-dioximatocobalt complexes
in which the original bridging protons of the
thiophenoxyphenylglyoxime (H2L') and 4,4'-thio-
bis(phenylglyoxime)dioxime (H4L''), transition metal
complexes of H2L' and H4L'', and the BF+2 capped Ni(II)
mononuclear complex of H2L'.
EXPERIMENTAL
4-Acetyldiphenyl sulfide and 4,4'-diacetyldiphenyl
sulfide were prepared according to published methods
[15]. All starting materials were commercially avail-
able and were of reagent grade. The 1H NMR and 13C
NMR spectra and elemental analyses for carbon,
hydrogen, and nitrogen were carried out at the labora-
tories of the Scientific and Technical Research Council
.
of Turkey (TÜBI TAK). Infrared spectra were recorded
on a Perkin Elmer model 1605 FT-IR spectrophotome-
ter as KBr pellets. Metal contents in the compounds
were determined on a Varian, Vista AX CCD spectro-
photometer. Magnetic moments of the complexes were
measured using a Sherwood Scientific model MX1
Gouy magnetic susceptibility balance at room temper-
ature. The pH values were measured on a WTW pH,
537 pH meter.
1
The text was submitted by the authors in English.
184

SYNTHESIS AND CHARACTERIZATION
185
Synthesis of 4-isonitrosoacetyldiphenyl sulfide added to the reaction mixture. The continuation of the
(ketooxime) (HL). Pure sodium (0.92 g) was dis- reaction was similar as described for the preparation of
solved in 50 ml of absolute ethanol with cooling, and 4-isonitrosoacetyldiphenyl sulfide.Yield 1.60 g (49 %),
then butyl nitrite (2.34 g, 20 mmol) was added drop by mp 163°C.
drop to the mixture with stirring at about –5°C. Sub-
IR (ν, cm–1): 3249 ν(O–H), 3028 ν(C–Har), 2878
sequently, a solution of 4-acetyldiphenyl sulfide
ν(C–Haliph), 2380 ν(O–H···O)chelate, 1619 ν(C = N),
(4.56 g, 20 mmol) in 35 ml of ethanol–water (2 : 1)
1007 ν(N–O).
mixture was added to the previous mixture with stir-
ring. The mixture was then left overnight at room tem-
1H NMR (δ, ppm): 9.28 (s., 2H, OH), 7.30–7.14
(d.d., J = 8.20 Hz, 4H, C–Har), 8.11 (s., 2 H, C–Haliph).
perature for the precipitate to form. The precipitated
substance was filtered followed by washing with
ether, dissolved in the minimum amount of water, and
reprecipitated by the addition of dilute HCl. The pre-
cipitate was filtered and recrystallized in ethanol–
water (1 : 1). The crystallized product was filtered,
washed with water, and dried in a vacuum oven at
50°C. Yield 2.72 g (53 %), mp 108°C.
13C NMR (δ, ppm): 147.2 (C1), 126.2 (C2), 127.3
(C3), 135.7 (C4), 164.2 (C5), 157.0 (C6).
Synthesis
of
4,4'-thio-bis(phenylglyoxime)
(dioxime) (H4L''). Bis(ketooxime) (1.31 g, 4.0 mmol)
was dissolved in 50 ml of a chloroform–ethanol (1 : 1)
mixture. Subsequently, solutions of NH2OH · HCl (0.55 g,
8 mmol) and CH3COONa (2.05 g, 2.5 mmol) were
added to the previous mixture with stirring. The reac-
tion mixture was refluxed for 12 h, and chloroform was
removed in vacuo. The precipitated material was fil-
tered and then recrystallized in anethanol–water (1 : 2)
mixture. Yield 0.96 g (67%), mp 219°C.
IR (ν, cm–1): 3240 ν(O–H), 3026 ν(C–Har), 2877
ν(C–Haliph), 2372 ν(O–H···O)chelate, 1631 ν(C=N), 1018
ν(N–O).
1H NMR (δ, ppm): 9.31 (s., 1H, OH), 7.25–6.98
(d.d., J = 11.0 Hz, 4H, C–Har), 7.29–7.15 d.t.t. (J = 8.78 Hz,
5H, C–Har), 8.18 (s., 1 H, C–Haliph).
IR (ν, cm–1): 3277 ν(O–H), 3017 ν(C–Har), 2874
ν(C–Haliph), 2372 ν(O–H···N)chelate, 1693 ν(C=N), 988
ν(N–O).
1H NMR (δ, ppm): 9.02 (s., 2H, OHa), 8.27 (s., 2H,
OHb), 7.18–6.96 (d.d., J = 8.40 Hz, 4H, C–Har), 8.20
(s., 2H, C–Haliph).
13C NMR (δ, ppm): 124.0 (C1), 126.7 (C2), 119.6
(C3), 147.5 (C4), 147.7 (C5), 120.5 (C6), 127.6 (C7),
135.9 (C8), 164.3 (C9), 157.1 (C10).
Synthesis of 4-thiophenoxyphenylglyoxime
(dioxime) (H2L'). 4-Isonitrosoacetyldiphenyl sulfide
(2.57 g, 10 mmol) was dissolved in 50 ml of ethanol.
Subsequently, solutions of NH2OH · HCl (0.77 g,
11 mmol) and CH3COONa (2.62 g, 32 mmol) (dis-
solved in the minimum amount of water) were added
with stirring. The reaction mixture was refluxed for 4 h,
and then excess ethanol in the reaction mixture was
removed in vacuo. The precipitate was filtered and then
recrystallized in an ethanol–water (1 : 2) mixture.Yield
1.87 g (69 %), mp 169°C.
13C NMR (δ, ppm): 147.0 (C1), 125.9 (C2), 126.9
(C3), 135.4 (C4), 155.7 (C5), 156.8 (C6).
Synthesis of the Cu(II), Ni(II) and Co(II) com-
plexes of the dioximes. 4-Thiophenoxyphenylgly-
oxime (0.54 g, 2.0 mmol) or 4,4'-thio-bis(phenylgly-
oxime) (0.36 g, 1.0 mmol) was dissolved in 30 ml of hot
ethanol. Then a solution of (1.00 mmol) Cu(NO3)2 ·
2H2O, NiCl2 · 6H2O or Co(NO3)2 · 6H2O (2 : 1) in 20 ml
of a water–ethanol mixture was added drop by drop
IR (ν, cm–1): 3247 ν(O–H), 3023 ν(C–H‡r),
2908 ν(C–Haliph), 2376 ν(O–H···N)chelate, 1692 ν(C=N), with stirring. The pH of the reaction mixture was
around 3.5–4.0 and was then adjusted to 5.5–6.0 by
adding a 1% NaOH solution. The precipitated complex
was kept in a water bath at 60°C for 1 h in order to com-
plete the precipitation. The precipitate was filtered off,
washed with water, ethanol, and diethyl ether, and
dried.
Synthesis of [(L'BF2)2Ni]. A suspension of
(HL')2Ni (0.3 g, 0.5 mmol) in 50 ml of freshly dis-
tilled dry acetonitrile was brought to the reflux tem-
perature in a nitrogen atmosphere. An equivalent
978 νe(N–O).
1H NMR (δ, ppm): 9.07 (s., 1H, OHa), 8.62 (s., 1H,
OHb), 7.22–7.01 (d.d., J = 10.7 Hz, 4H, C–Har), 7.28–
7.11 (d.t.t., J = 8.59 Hz, 5H, C–Har), 8.13 (s., 1 H, C–
Haliph).
13C NMR (δ, ppm): 123.7 (C1), 126.5 (C2), 119.4
(C3), 147.2 (C4), 147.6 (C5), 119.3 (C6), 122.7 (C7),
135.8 (C8), 156.7 (C9), 156.8 (C10).
Synthesis of 4,4'-diisonitrosoacetyldiphenyl sul-
fide [bisketooxime)] (H2L). Pure sodium (0.58 g) was amount of boron-trifluoride etherate complex
(0.41 ml) was added with continuous stirring to this
suspension, which changed its color to red immedi-
ately. After refluxing for 30 min, the solvent was
evaporated to dryness. Then the dark red crude prod-
dissolved in 50 ml of absolute ethanol with cooling, and
then butyl nitrite (2.93 g, 25 mmol) was added drop by
drop to the mixture with stirring at about –5°C. Subse-
quently, a solution of 4,4'-diacetyldiphenyl sulfide
(2.70 g, 10 mmol) in 50 ml of ethanol–water (2 : 1) was uct was dissolved in 10 ml of dry acetonitrile and
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 33 No. 3 2007

S¸
CO KUN, KOÇ
186
allowed to stand in a refrigerator at –18°C overnight,
whereupon the compound crystallized from the solu-
tion. The red crystallized product was collected by
filtration, washed with cold acetonitrile and diethyl
ether, and then dried in vacuo.
RESULTS AND DISCUSSION
4-Acetyldiphenyl sulfide and 4,4'-diacetyldiphenyl
sulfide were obtained by the reaction of acetyl chloride
with diphenyl sulfide in the presence of AlCl3 as cata-
lyst in the Friedel–Crafts reaction [15]. Ketooximes
(HL and H2L) and dioximes (H2L' and H4L'') of these
compounds were originally synthesized by a described
procedure [16]. The structures of keto-oximes and
dioximes (ligands) are given bellow:
The colors, yields, melting points, elemental analy-
sis, and FT-IR data, magnetic moments of these com-
pounds are given in Tables 1 and 2, respectively.
2
3
6
7
O
O
C4H9ONO/C2H5ONa
1
S
C
S
C
8
9
4
5
10
CH3
C
NOH
2
3
6
7
H
(HL)
2
2
3
3
6
6
7
NOHb
NH2OH · HCl/CH3COONa
1
S
C
8
HL
4
5
10C NOHa
9
7
H
(H2LI)
3
2
2
3
O
O
O
O
C4H9ONO/C2H5ONa
4
4
C
S
C
C5
S
C
5
1
1
H3C
CH3
6
C
NOH
6
HON
C
3
2
2
3
H
H
(H2L)
3
3
2
2
2
3
NOHb
6 C NOHa
bHON
NH2OH · HCl/CH3COONa
4
4
(H2L)
C
6
S
C
5
1
1
5
aHON
C
2
3
H
H
(H2LII)
In the 1H NMR spectra of the oximes, two peaks are
present for the OH protons of the dioxime groups (H2L'
and H4L''), while the OH protons of the ketooximes (HL
and H2L) appear as singlet peaks. When the chemical shift
values of the two OH groups in the dioximes are com-
pared, those in the lower field quite closely resemble each
other (9.07–9.02 ppm), while a considerable difference is
observed for those in the higher field (8.62–8.27 ppm) [17,
18]. The chemical shifts of the C–H protons adjacent to
All the signals in the 147.7–119.4 ppm range are
assigned to the carbon atoms of the aromatic rings. All
these values are in agreement with those reported pre-
viously [20].
The FT-IR data for characterizing the structures of
the complexes are given in Table 2. In the FT-IR spectra
of the oximes, O–H stretching vibrations appear as a
broad absorption at 3277–3240 cm–1. Bands due to C=N
and N–O stretches appear at 1693–1619 and 1018–
the oxime groups and the aromatic protons are in a range 978 cm–1, respectively. These absorption data are in
of 8.20–8.11 and 7.30–6.96 ppm, respectively. All these agreement with those previously reported for other
values are in agreement with the chemical shift values of oxime derivatives [21, 22]. Bands appearing at 2380–
2372 cm–1 in the ketooximes and dioximes indicate that
there are intermolecular H-bridges.
oxime protons [19, 20].
13
In the C NMR spectrum of the ligands (H2L' and
H4L''), the signals at 156.8–156.7 and 156.8–155.7 ppm
are attributed to the carbon atoms of the oxime groups,
respectively. In the 13C NMR spectrum of the ligands
(HL and H2L), the signals at 164.3–164.2 and 157.1–
157.0 ppm are attributed to the carbonyl carbon atom
and the carbon atom of the oxime group, respectively.
O
H
N H
O H
R
C
O
R
C
O
HC
Dioxime
N
HC
Ketooxime
N
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SYNTHESIS AND CHARACTERIZATION
187
The Cu(II), Ni(II), and Co(II) complexes of the tions, respectively [23]. This complex exhibits upward
oximes were obtained in an ethanol–water (1 : 1) mix- shifts in the stretching vibrations of the azomethine
groups, owing to the BF2 groups [24].
ture by the addition of sufficient 1% NaOH to increase
the pH to 5.0–5.5. Some physical properties of the com-
plexes are given in Tables 1 and 2. The structures of the
complexes were characterized by FT-IR, elemental
analysis, and magnetic measurements. 1H NMR spectra
of the complexes could not be taken because of their
very low solubility in organic solvents. In the FT-IR
spectra of the complexes, the shifts of the C=N stretch-
ing frequency to lower frequency and the vibration cor-
responding to the N–O band to higher frequency indi-
cate the formation of coordination bonds between the
metal and nitrogen atoms of the dioximes. The weak
bands appearing around 1737–1719 cm–1 in the FT-IR
spectra of the complexes correspond to intermolecular
hydrogen bridges (O–H···O), but these peaks are miss-
ing in the spectra of the ligands. In addition, the broad
peaks appearing around 3418–3391 cm–1 in the spectra
of the Co(II) complexes indicate that H2O is coordi-
nated to Co(II).
When the elemental analyses of the complexes were
carried out, the metal–ligand ratios were found to be
1 : 2 in the complexes of 4-thiophenoxyphenylgly-
oxime and 1 : 1 in the polymeric complexes of 4,4'-thio-
bis(phenylglyoxime). The molecular weights of poly-
meric metal complexes of 4,4'-thio-bis(phenylgly-
oxime) could not be determined because of their insol-
ubility in organic solvents. The Ni(II) and Cu(II) com-
plexes with the ligands H2L' and H4L'' are diamagnetic.
The room temperature magnetic moments of the Co(II)
complexes with the ligands H2L' and H4L'' are paramag-
netic with magnetic susceptibility values of 3.93 and
3.98 µB, respectively. The effective magnetic moments
of the octahedral Co(II) complexes were 4.10 and
4.30 µB, respectively [25]. The magnetic data of the
Co(II) complexes agree with a d7 metal ion in a square-
planar field or an octahedral configuration [26, 27].
According to the FT-IR data, elemental analysis,
and magnetic measurements, the Ni(II) and Cu(II)
complexes have a square-planar structure, whereas the
Co(II) complexes have an octahedral structure. Mag-
netic susceptibility measurements of the complexes
provide information regarding their structures and are
shown in Table 2. The structures of the obtained com-
The [(L'BF2)2Ni] complex was prepared from boron
trifluoride and complex [(HL')2Ni] in acetonitrile. In
the FT-IR spectrum of [(L'BF2)2Ni], the broad band at
1722 cm–1 due to O–H···O bending vibrations disap-
peared upon encapsulation of the hydrogen-bridged
complex with BF2 with the concomitant appearance of
peaks at 1162 and 832 cm–1 for the B–O and B–F vibra- plexes are given bellow:
O
N
H O
N
H
C
C
S
C
C
M
S
N
N
O
H
O H
Octahedral and square-planar structures of the metal complexes
OH2
Co(II)
OH2
of 4-thiophenoxyphenylglyoxime; M = Ni(II), Cu(II), and
.
O
N
H O
N
H
C
C
S
C
C
M
N
N
O
H
n
O H
Octahedral and square-planar structures of the metal complexes of 4,4'-thio-
OH2
bis(phenylglyoxime); M = Ni(II), Cu(II), and
Co(II)
OH2
.
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CO KUN, KOÇ
188
F
F
B
O
O
H
N
N
C
C
S
C
C
Ni
S
N
N
H
O
O
B
F
F
Square-planar structure of the BF+-capped Ni(II) mononuclear
2
complex of 4-thiophenoxyphenylgyoxime.
Table 1. The elemental analysis data and some physical properties of ketooximes, glyoximes, and its complexes
Content (found/calcd), %
M.p., Yield, g
Compound
Empirical formula
Color
°C
(%)
C
H
N
metals
HL
H L'
C14H11NO2S
White 108 2.72 (53) 65.29/65.36 4.23/4.28 5.39/5.44
Cream 169 1.87 (69) 61.68/61.76 4.33/4.41 10.22/10.29
Cream 163 1.60 (49) 58.47/58.53 3.59/3.65 8.45/8.53
Yellow 219 0.96 (67) 53.54/53.63 3.83/3.91 15.55/15.64
C14H12N2O2S
C16H12N2O4S
C16H14N4O4S
C28H22N4O4S2Cu
C28H22N4O4S2Ni
2
H L
2
H L"
4
[(HL')2Cu]
[(HL')2Ni]
[(L'BF2)2Ni]
Green >300 1.03 (85) 55.39/55.48 3.57/3.63 9.15/9.24 10.44/10.49
Red
>300 1.04 (87) 55.86/55.93 3.57/3.66 9.21/9.32 9.68/9.77
285* 0.98 (75) 48.18/48.11 3.09/3.15 7.93/8.02 8.32/8.40
C28H20N4O4S2B2F4Ni Red
[(HL')2Co(H O)2] C28H26N4O6S2Co
Brown >300 1.09 (86) 52.64/52.75 3.99/4.08 8.68/8.79 9.18/9.25
Green >300 0.35 (83) 45.69/45.76 2.77/2.86 13.23/13.34 15.08/15.14
2
[(H L")Cu]n
[C16H12N4O4SCu]n
[C16H12N4O4SNi]n
2
[(H L")Ni]n
Red
>300 0.35 (85) 45.88/45.96 2.79/2.87 13.32/13.40 13.98/14.05
2
[(H L")Co(H O)2]n [C16H16N4O6SCo]n
Brown >300 0.38 (84) 42.48/42.57 3.50/3.54 12.33/12.42 19.97/13.07
2
2
* Decomposition point.
Table 2. Data of magnetic measurements and characteristic IR spectra of the complexes
Compound Empirical formula µeff, µB ν(H O) ν(C–H)Ar ν(C–H)Aliph ν(C=N) ν(N–O) ν(O···H–O)
2
[(HL')2Cu]
C28H22N4O4S2Cu
C28H22N4O4S2Ni
Dia
Dia
3009 w* 2800 m*
1654 s*
1656 s
1675 s
1647 s
1648 s
1664 s
1653 s
989 s*
1003 s
985 s
1720 s
1722 s
[(HL')2Ni]
3018 w
3015 w
2885 m
2880 m
2938 m
2918 m
2927 m
2937 m
[(L'BF2)2Ni]
C28H20N4O4S2B2F4Ni Dia
[(HL')2Co(H O)2] C28H26N4O6S2Co
4.93
Dia
3418 s 3044 w
3024 w
1008 s
1004 s
994 s
1737 s
1723 s
1719 s
1727 s
2
[(H L")Cu]n
[C16H12N4O4SCu]n
[C16H12N4O4SNi]n
2
[(H L")Ni]n
Dia
3029 w
2
[(H L")Co(H O)2]n [C16H16N4O6SCo]n
4.98
3391 s 3048 w
1010 s
2
2
* s—strong, m—medium, w—weak.
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 33 No. 3 2007

SYNTHESIS AND CHARACTERIZATION
189
The above values of FT-IR, 1H NMR, 13C NMR, ele-
mental analysis, data and magnetic susceptibility are in
agreement with those previously reported, particularly
those of bis(phenylglyoxime) [28] and other glyoximes
[17, 21, 25].
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ACKNOWLEDGMENTS
15. Szmant, H.H. and Palopoli, F.P., J. Am. Chem. Soc.,
1950, vol. 72, no. 4, p. 1757.
This study was supported by the Scientific Research
Projects Coordinator of Selcuk University (Konya, Tur-
key), project no. 2001–029.
16. Burakevich, J.V., Lore, A.M., and Volpp, G.P., J. Org.
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