Synthesis and characterization of a new dioxime: Thermal and magnetic behavior of its heterotrinuclear BF+2-capped complexes

Article abstract of DOI:10.1080/00958972.2010.501106

New heterotrinuclear complexes have been obtained from dinuclear Fe(III) oxygen-bridged N,N'-bis(salicylidene)ethylenediamine (salenH₂) and bis(salicylidene)-o-phenylenediamine (salophH2) and Co(II), Ni(II), Cu(II) salts. Then, heterotrinuclear vic-dioxime complexes containing [image omitted] caps have been synthesized. The complexes have been characterized as low-spin distorted octahedral Fe(III) bridged by COO- groups. The structure of dioxime and its complexes were identified by using elemental analysis, magnetic susceptibility, thermal analysis, ICP-AES, 1H-NMR, and IR spectral data.

Full text of DOI:10.1080/00958972.2010.501106

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Synthesis and characterization of a
new dioxime: thermal and magnetic
behavior of its heterotrinuclear -
capped complexes
Şaban Uysal a
a Department of Chemistry, Faculty of Science , Selcuk
University , 42031 Konya, Turkey
Published online: 14 Jul 2010.
To cite this article: Şaban Uysal (2010) Synthesis and characterization of a new dioxime: thermal
and magnetic behavior of its heterotrinuclear -capped complexes, Journal of Coordination
Chemistry, 63:13, 2370-2378, DOI: 10.1080/00958972.2010.501106
To link to this article: http://dx.doi.org/10.1080/00958972.2010.501106
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Journal of Coordination Chemistry
Vol. 63, No. 13, 10 July 2010, 2370–2378
Synthesis and characterization of a new dioxime: thermal
and magnetic behavior of its heterotrinuclear
BFY2 -capped complexes
Sꢀ ABAN UYSAL*
Department of Chemistry, Faculty of Science, Selcuk University,
42031 Konya, Turkey
(Received 11 November 2009; in final form 2 April 2010)
New heterotrinuclear complexes have been obtained from dinuclear Fe(III) oxygen-bridged
N,N0-bis(salicylidene)ethylenediamine (salenH2) and bis(salicylidene)-o-phenylenediamine
(salophH2) and Co(II), Ni(II), Cu(II) salts. Then, heterotrinuclear vic-dioxime complexes
containing BFþ2 caps have been synthesized. The complexes have been characterized as low-spin
distorted octahedral Fe(III) bridged by COOꢀ groups. The structure of dioxime and its
complexes were identified by using elemental analysis, magnetic susceptibility, thermal analysis,
ICP-AES, 1H-NMR, and IR spectral data.
Keywords: BFþ2 -capped complex; vic-dioximes; Transition metal complexes; Salen/saloph
1. Introduction
Polydentate coordination of ligands leads to the formation of homo or
heteropolynuclear complexes with cations in the metallo-macrocyclic cavity, opening
design of macrocycle ligands containing additional donors within the N4 chain and
hydroxyimino nitrogen donors of dioximes. The incorporation of vic-dioximes onto the
macrocycle provides an efficient binding site for the transition metal cations by the
formation of an MN4 core with two additional hydrogen bridges [1–3]. The presence of
mildly acidic hydroxyl groups and slightly basic nitrogens causes vic-dioximes to be
amphoteric ligands which form corrin-type square-planar, square-pyramidal,
and octahedral complexes with transition metal cations such as Ni(II), Cu(II), and
Co(II) [4–7].
Synthetic macrocycles have been known for over 75 years, although many
publications in this area occurred in the late 1960s [8, 9] when more than 5000
macrocyclic compounds were reported; since then the number has increased markedly
from year to year. Some of these compounds were recognized as promising analytical
reagents [10, 11]. One of the best strategies for designing and preparing polynuclear
*Email: uysal77@hotmail.com; uysal77@gmail.com
Journal of Coordination Chemistry
ISSN 0095-8972 print/ISSN 1029-0389 online ꢁ 2010 Taylor & Francis
DOI: 10.1080/00958972.2010.501106

Heterotrinuclear BFþ2 -capped complexes
2371
species is to use mononuclear complexes as ligands which contain potential donor sites
for other metal ions.
Magnetochemical properties of the m-oxo-bridged complexes [{Fe(salen)}2O]
(salenH2 ¼ N,N0-bis(salicylidene)ethylenediamine) and [{Fe(saloph)}2O] [saloph-H2 ¼
bis(salicylidene)-O-phenylenediamine] have been proven, and their properties and
X-ray studies are published [12–18].
Gok et al. [19–21] recently reported studies of the coordinating ability of new
¨
vic-dioximes containing macrocyclic units. We are currently interested in the design of
new ligands and ligand complexes which can serve as efficient chelating
agents toward metal cations [22–24]. In our previous studies, we synthesized and
characterized BFþ2 -capped heterotrinuclear complexes, tripodal [Fe(salen/salophen)]-
capped melamine-based trinuclear complexes [25–29].
We are also interested in heterotrinuclear systems formed by 4-carboxyanilinophe-
nylglyoxime bridges because no satisfactory work dealing with this bridge
and associated data have appeared in the literature. We have prepared an amino
vic-dioxime containing a diaza-dioxa macrocyclic unit and some of its heterotrinuclear
complexes.
2. Experimental
Acetophenone 1 and all solvents were purchased from Merck. !-Isonitrosoacetophenone
2 [30], anti-phenylglyoxime 3 [31], anti-chlorophenylglyoxime 4 [30], [{Fe(saloph)}2O],
and [{Fe(salen)}2O] [32] were synthesized according to the literature procedures.
Some reactions were carried out under dry argon. Melting points were measured
using a Buchi SMP-20 melting point apparatus. Elemental analyses (C, H, and N) were
1
determined using a Leco, CHNS-932 model analyzer. H-NMR spectra were recorded
on a Bruker DPX-400 400 MHz high-performance digital FT-NMR and IR spectra
on a Perkin-Elmer 1605 FT-IR spectrometer in KBr pellets (4000–440 cmꢀ1).
Thermal analyses were performed on Shimadzu DTA 50 and TG 50 H models using
10 mg samples. The differential thermal analysis (DTA) and thermꢀa1l gravimetric
analysis (TG) curves were obtained at a heating rate of 10ꢁC min
from 22ꢁC
to 750ꢁC under dry nitrogen. The magnetic susceptibilities of metal samples
were determined using a Sheerwood Scientific MX Gouy magnetic susceptibility
apparatus and magnetic measurements were carried out using the Gouy method
with Hg[Co(SCN)4] as calibrant. The effective magnetic moments, meff, per metal were
pffiffiffiffiffiffi
calculated from the expression: ꢀeff ¼ 2:84 ꢁMT B.M., where ꢁM is the molar
susceptibility. The metal and boron contents of each complex were determined on
a Varian, Vista AX CCD simultaneous model ICP-AES spectrophotometer. The
product mixture at the end of the reaction was separated using Combi Flash
Chromotography.
2.1. 4-Carboxyanilinophenylglyoxime (H3L)
A solution of 4-carboxyanilin (1.4 g, 10.0 mmol) dissolved in 10 mL of benzene was
added dropwise to a suspension of chlorophenylglyoxime (2.0 g, 10.0 mmol) dissolved in

2372
Sꢀ . Uysal
10 mL of benzene, and the mixture was stirred for 40 h under argon. The
solvent was evaporated and the precipitated solid product was filtered and dried.
LC-MS (ESIþ) m/z ¼ 299.09 [100%, 4-carboxyanilinophenylglyoxime (H3L)].
Molecular peaks of the compounds are observed with the same isotope distribution
as the theoretical ones.
2.2. Synthesis for [H2Lsalen/saloph]Fe(III) complexes (6a, 6b)
A solution of 4-carboxyanilinophenylglyoxime (0.30 g, 1.00 mmol) dissolved in
10 mL of absolute methanol was added dropwise to a suspension of [{Fe(salen)}2O]
(0.33 g, 0.50 mmol) or [{Fe(saloph)}2O] (0.38 g, 0.50 mmol) dissolved in 10 mL of
absolute methanol, and the mixture was stirred and refluxed for 2 h under argon. A
distinct change in color and decrease in pH (2.5–2.8) was observed. While an
equivalent of methanolic solution of NaOH (0.1 M) was added dropwise to adjust pH
to 5.5, the mixture was stirred and heated to 60ꢁC on a water bath for 2 h.
The precipitated solid product was cooled to room temperature and filtered,
washed with water, ethanol, and diethylether, and dried in a vacuum cabinet.
LC-MS (ESIþ) m/z ¼ 619.85 [100%, 6a], MS (ESIþ) m/z ¼ 667.85 [100%, 6b].
Molecular peaks of the cations are observed with the same isotope distribution as the
theoretical ones.
hu
–
O
2.3. Synthesis for Ni(II), Cu(II) and Co(II) complexes of (6a, 6b)
A suspension of (6a, 6b) (1.24–1.34 g, 2.00 mmol) was prepared in hot ethanol (20 mL).
Solution of 1.00 mmol NiCl2 ꢂ 6H2O, CuCl2 ꢂ 2H2O, CoCl2 ꢂ 6H2O in 10 mL ethanol
was added dropwise with stirring to the suspension. The pH of the reaction mixture was

Heterotrinuclear BFþ2 -capped complexes
2373
3.5–4.0 and was then adjusted to 5.5–6.0 by adding 1% NaOH solution. The
precipitated complex was kept on a water bath at 60ꢁC for 1 h to complete precipitation.
The precipitated solid product was cooled to room temperature, filtered, washed
with water, ethanol and diethylether, and dried in vacuum. LC-MS (ESIþ)
m/z ¼ 1392.39 [100%, 7b], LC-MS (ESIþ) m/z ¼ 1337.25 [100%, 8a], and LC-MS
(ESIþ) m/z ¼ 1428.63 [100%, 9b]. Molecular peaks of the cations are observed with the
same isotope distribution as the theoretical ones.
H
O
N
N
O
N
O
N
H
N
O
O
R
L
M
L
Fe
Ethanol
O
MCl .nH O
2
(6a, 6b)
+
2
2
O
Fe
O
O
O
N
N
N
O
N
H
N
O
R
M: Ni(II) (7), Cu (II) (8), Co(II) (9)
H
R
(7a, 7b, 8a, 8b, 9a, 9b)
–CH2CH2–
(a)
(b)
L=H2O for
8 and 9
2.4. Synthesis of [Fe(III)(BF2Lsalen/saloph)2Ni(II)/Cu(II)/CoII)] complexes
(10a, 10b, 11a, 11b, 12a, 12b)
Suspensions of [Fe(III)(HLsalen/saloph)2Ni(II)/Cu(II)/CoII)] (1.00 mmol) in 40 mL of
dry acetonitrile were stirred at room temperature in argon for 30 min and an equivalent
of boron-trifluoride etherate (0.82 mL) was added with continuous stirring to this
suspension, which changed to yellow color immediately. After stirring for 2 h, during
which color changed to dark red, the solvent was evaporated to dryness. The dark red
crude products were dissolved in 10 mL dry diethyl ether and allowed to stand in a
refrigerator at ꢀ18ꢁC overnight, whereupon the compounds precipitated from the
solution. The dark red powders were collected by filtration, washed with cold diethyl
ether and then dried in vacuum. LC-MS (ESIþ) m/z ¼ 1391.97 [100%, 10a], LC-MS
(ESIþ) m/z ¼ 1528.83 [100%, 11b], and LC-MS (ESIþ) m/z ¼ 1428.21 [100%, 12a].
Molecular peaks of the cations are observed with the same isotope distribution as the
theoretical ones.
F
F
CH3CN
B
O
Fe
O
2
(7a, 7b, 8a, 8b, 9a, 9b)
2 BF3.O(C2H5)2
+
N
N
O
N
O
H
N
O
O
R
L
N
M
O
M: Ni(II) (10), Cu (II) (11), Co (II) (12)
O
O
N
N
N
H
N
O
L
N
O
Fe
R
R
O
B
–CH2CH2–
(a)
(b)
F
F
(10a, 10b, 11a, 11b, 12a, 12b)
L= H2O for 11 and 12

2374
Sꢀ . Uysal
3. Results and discussion
3.1. 1H NMR spectrum interpretation of ligands
The target ligand 5 was synthesized in a four-step sequence from acetophenone.
The conversion of 1 to the keto oxime derivative 2 was accomplished in 74% yield [30]. In
the 1H-NMR spectrum of 2, the presence of singlets at ꢂ ¼ 8.40 and 11.50 ppm showed the
keto oxime. This compound was easily converted to the glyoxime derivative 3 by the
reaction with hydroxylamine [31] in 92% yield. 1H-NMR spectra of 3 with two singlets
at ꢂ ¼ 11.6 and 11.4 ppm showed glyoxime. Chlorophenylglyoxime [30] 4 was obtained
from the reaction with chlorine in 86% yield. In the 1H-NMR spectrum of 4, the absence
of a singlet at ꢂ ¼ 8.40 ppm showed the formation of chlorophenylglyoxime.
4-Carboxyanilinophenylglyoxime, 5, was prepared by reacting 4-aminobenzoic acid
with chlorophenylglyoxime. Resonances at 11.62 and 11.23 ppm are the OH protons of
the oxime groups. These two deuterium-exchangeable singlets correspond to two
nonequivalent OH, indicating that the anti-configuration of OH groups are relative to
each other [33, 34]. In 1H-NMR spectra of 5, a broad signal at 13.08 ppm was assigned to
the acidic OH. The NH proton was at 8.52 ppm and the aromatic C–H protons were at
6.61–7.63 ppm. 1H-NMR spectrum of the complexes could not be taken because of their
paramagnetic character. NMR spectra are in good agreement with the previous reports
[35, 36].
3.2. FT-IR spectrum interpretation of ligands and complexes
In FT-IR spectra of 5 bands at 3375, 3268, 1644, 1410, and 998 cmꢀ1 were, respectively,
assigned to (NH), (O–H), (C¼N), (COOꢀ), and (N–O) stretching vibrations [37–42].
In 6a and 6b, vibrations at 1572–1583, 1635–1628, and 993–997 cmꢀ1 were assigned to
ꢃ(C¼N) (for N2O2O2 compartment) [38, 39], (C¼N)oxime, and (N–O) vibrations,
respectively. In FT-IR spectra of 7a, 7b, 8a, 8b, 9a, and 9b, shift of the N–O band to
higher frequency indicates the formation of bonds between metal and nitrogen of the
dioximes [43]. In 7a, 7b, 8a, 8b, 9a, and 9b, N–H stretching vibrations were observed at
3337–3343 cmꢀ1 [38]; downward shifts of 23 cmꢀ1 for the C¼N absorption indicated
coordination through nitrogen [38, 39, 43, 44]. It seems that salen (or saloph) has been
linked from carboxylate of the ligand. In all complexes, peaks at 1320–1360 cmꢀ1
(phenolic C–O stretching vibrations) of salen and saloph ligands are seen at
1286–1288 cmꢀ1 [38, 39]. The BFþ2 -bridged complexes (10a, 10b, 11a, 11b, 12a, and
12b) exhibited a shift to about 1658 cmꢀ1 for the (C¼N)oxime absorption and to about
1065 cmꢀ1 for the N–O absorption. The broad band at 1715–1723 cmꢀ1 assigned to
the O–H ꢂ ꢂ ꢂ O bending vibrations disappeared upon the insertion of the BF2þ
with the simultaneous appearance of peaks at 1171–1175 and 872–875 cmꢀ1 for
B–O and B–F resonances, respectively. Broad bands at 3511–3525 cmꢀ1 were attributed
to the H2O bands as axial ligands for Co(II) and Cu(II) complexes. These absorption
data are in good harmony with those previously reported for substituted vic-dioximes
[33–36, 43, 44] (table 1).

Heterotrinuclear BFþ2 -capped complexes
Table 1. Characteristic FT-IR bands (cmꢀ1) of complexes.a
FT-IR data of compounds (ꢃmax/cmꢀ1
C¼Nox C¼N N–H OHO N–O M–N M–O B–O B–F
2375
)
Compound (empirical formula)
C
31H26FeN5O6
C35H26FeN5O6
(6a)
(6b)
(7a)
(7b)
(8a)
(8b)
(9a)
(9b)
(10a)
(10b)
(11a)
(11b)
(12a)
(12b)
1635
1628
1612
1605
1614
1606
1613
1608
1657
1658
1654
1657
1656
1658
1572 3344
1583 3346
1582 3343
1576 3338
1584 3339
1587 3337
1586 3343
1589 3342
1585 3342
1584 3339
1586 3340
1587 3338
1585 3345
1583 3344
1712
1713
993
997
535
536
533
535
536
536
536
537
538
535
536
537
534
533
474
475
475
472
476
477
476
471
477
474
476
472
478
473
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
C62H50Fe2N10O12Ni
C70H50Fe2N10O12Ni
1715 1035
1714 1028
1714 1033
1716 1029
1718 1035
1722 1027
–
–
–
–
–
–
C62H54Fe2N10O14Cu
C70H54Fe2N10O14Cu
C62H54Fe2N10O14Co
C70H54Fe2N10O14Co
C62H48Fe2N10O12NiB2F4
C70H48Fe2N10O12NiB2F4
C62H52Fe2N10O14CuB2F4
C70H52Fe2N10O14CuB2F4
C62H52Fe2N10O14CoB2F4
C70H52Fe2N10O14CoB2F4
1066
1063
1064
1065
1061
1065
1172 872
1171 874
1172 875
1175 874
1173 873
1175 875
aKBr pellet.
3.3. Magnetic measurements of complexes
Best evidence for the proposed structures of the heteronuclear complexes comes from
magnetic measurements. For Fe(III) complexes such as (salen or salophen)Fe(III),
magnetic moments depend greatly upon the axial ligands. Many reports state that
Fe(III) exhibits high spin (S ¼ 5/2), if only one oxygen donor coordinates to Fe(III) of
salen or salophen complexes [32, 45]. We report here that if COOꢀ ion coordinates to
Fe(III) of salen or salophen through both oxygens, Fe(III) exhibits low spin (S ¼ 1/2)
[25–29, 46–48]. Where the starting complexes [H2Lsalen/saloph]Fe(III) are octahedral
d5 (paramagnetic), any magnetic moment of the heteronuclear species should arise from
the occupation of N2O2O2 compartment [25]. On this assumption, the observed
magnetic moments for the heterotrinuclear complexes are those for isolated d5 systems
(S ¼ 1/2). Thus, heterotrinuclear complexes 7a, 7b, 8a, 8b, 9a, and 9b 1 : 2
(metal : starting complexes) ratio were obtained throughout the reaction of starting
complexes (6a, 6b) with Ni(II), Co(II), and Cu(II). Values of 1.85–1.84–1.85–1.86 B.M.
for 7a, 7b, 10a, and 10b, respectively, which are same as the starting complexes
(1.85 B.M.) for magnetic measurement per Fe(III), shows that the Ni(II) compounds are
square-planar d8 (S ¼ 0 ꢃ 1/2) (diamagnetic). The values of 1.74–1.76 and 1.72–1.74
B.M. for 8a, 8b, 11a, and 11b, respectively, show that the Cu(II) containing compounds
have t62ge3g (S ¼ 1/2). The values of 3.55–3.61 and 3.49–3.57 B.M. for 9a, 9b, 12a, and
12b, respectively, of magnetic measurement per atom of heterotrinuclear complexes
show that Co(II) containing compounds are represented by the electronic structure t52ge2g
(S ¼ 3/2). The magnetic data for the Cu(II) and Co(II) complexes show good harmony
with the d9 and high-spin d7 distorted octahedral metal ion for the complexes of both
Cu(II) and Co(II) [25–29, 46–48]. Magnetic susceptibility measurements are presented
in table 2. This conclusion is supported by elemental analyses, suggesting that trinuclear
Co(II) and Cu(II) complexes also have octahedral, while trinuclear Ni(II) complexes
have two octahedral and a square-planar structure.

2376
Sꢀ . Uysal

Heterotrinuclear BFþ2 -capped complexes
3.4. Thermal analysis interpretation of complexes
2377
Complex 12b was selected for the investigation of thermal properties. The thermal
analyses (TG, DTA) of 12b showed weight loss of 6.25% in the temperature range
75–180ꢁC, corresponding to the loss of BFþ2 . The thermal decomposition of 12b starts in
the range of 210–390ꢁC by the weight loss of 5.74% from CO2, and organic group
decomposition is complete in the range of 440–580ꢁC by the weight loss of 61.63%.
The final decomposition products were metal oxides. The observed weight loss for 12b
is in good harmony with calculated values [26–29, 46].
3.5. Mass spectral data interpretation of complexes of all ligand and complexes
Some complexes were investigated by LC-MS (ESIþ) spectra. The calculated molecular
weights of all ligand and complexes have been given in table 2. The molecular peaks of
the cations are observed with the same isotope distribution as calculated, theoretically.
That is, from the investigation of LC-MS spectra of the compounds, it has been seen
that the molecular weights of ligands and complexes are in good harmony with the
intensity of observed values in LC-MS spectra.
4. Conclusions
Heterotrinuclear BFþ2 -capped complexes containing vic-dioxime were synthesized.
Synthetic strategy for preparing heterotrinuclear BFþ2 -capped complexes uses a complex
as a ‘‘ligand’’ that contains a potential donor capable of coordinating to the other
ligand. We have chosen [{Fe(salen/saloph)}2O] as ‘‘ligand complexes’’ because they
can coordinate to the other ligand. These complexes are examples of heterotrinuclear
BFþ2 -capped complexes bridged by carboxylate anions to the iron centers. Their
1
structures were characterized by elemental analysis, H NMR, FT-IR spectroscopy,
LC-MS, thermal analyses, and magnetic susceptibility measurements. The magnetic
data for the complexes show d5–d8–d5 (S ¼ 1/2–0–1/2), d5–d9–d5 (S ¼ 1/2–1/2–1/2), and
d5–d7–d5 (S ¼ 1/2–3/2–1/2) metal ion in octahedral–octahedral–octahedral structures
for Cu(II) and Co(II), octahedral–square planar–octahedral structures for Ni(II).
The other characterization methods, 1H NMR, FT-IR spectroscopy, LC-MS, and
thermal analyses confirm the suggested structures.
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