2-(N-tosylamino)benzaldehyde thiobenzoylhydrazone and its complexes with copper(II) and zinc(II): Synthesis and structures

Article abstract of DOI:10.1134/S107032841304009X

2-(N-Tosylamino)benzaldehyde thiobenzoylhydrazone and its copper(II) and zinc(II) complexes with dimethylformamide (DMF) and methanol, [CuL(DMF)] and [ZnL(CH₃OH)], respectively, were synthesized. The structures of the copper(II) complex and the

Full text of DOI:10.1134/S107032841304009X

ISSN 1070ꢀ3284, Russian Journal of Coordination Chemistry, 2013, Vol. 39, No. 5, pp. 367–372. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © L.D. Popov, S.I. Levchenkov, I.N. Shcherbakov, A.A. Tsaturyan, Yu.P. Tupolova, Z.A. Starikova, A.S. Burlov, V.V. Lukov, V.A. Kogan, 2013, published in
Koordinatsionnaya Khimiya, 2013, Vol. 39, No. 5, pp. 259–263.
2ꢀ(NꢀTosylamino)benzaldehyde Thiobenzoylhydrazone and Its
Complexes with Copper(II) and Zinc(II): Synthesis and Structures
L. D. Popova, S. I. Levchenkovb, *, I. N. Shcherbakova, A. A. Tsaturyana, Yu. P. Tupolovaa,
Z. A. Starikovac, A. S. Burlova, V. V. Lukova, and V. A. Kogana
a Southern Federal University, RostovꢀonꢀDon, 344104 Russia
b Southern Scientific Center, Russian Academy of Sciences, RostovꢀonꢀDon, Russia
c Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991 Russia
*eꢀmail: physchem@yandex.ru
Received August 14, 2012
Abstract—2ꢀ(NꢀTosylamino)benzaldehyde thiobenzoylhydrazone and its copper(II) and zinc(II) comꢀ
plexes with dimethylformamide (DMF) and methanol, [CuL(DMF)] and [ZnL(CH3OH)], respectively,
were synthesized. The structures of the copper(II) complex and the cyclic product of hydrazone oxidation
(1,3,4ꢀthiadiazole derivative) were determined by Xꢀray diffraction analysis.
DOI: 10.1134/S107032841304009X
INTRODUCTION
on a PerkinElmer 240C instrument at the Laboratory
of Microanalysis of the Southern Federal University.
Thioꢀcontaining hydrazine derivatives have long
ago attracted researchers’ attention as carriers of proꢀ
nounced biological activity [1–5] and complexation
ability [6–10]. Transition metal complexes with thioꢀ
hydrazones are also characterized by the high biologiꢀ
cal activity [3, 5, 11]. Compounds of this class are
The specific magnetic susceptibility of complex
determined by the relative Faraday method in the temꢀ
perature range from 77.4 to 300 using
Hg[Co(CNS)4] as a standard for calibration.
I was
K
Synthesis of H2L A hot solution of 2ꢀ(Nꢀtosylꢀ
.
interesting in the theoretical aspect due to the possibilꢀ amino)benzaldehyde (5 mmol) in ethanol (10 mL)
ity of the formation of various tautomeric forms in the was poured to a hot solution of thiobenzhydrazide
metal complexes. Many thiosemicarbazones of diverse (5 mmol) in ethanol (10 mL). Glacial acetic acid
carbonyl compounds are described, whereas data on (3 drops) was added to the obtained solution, and the
thioacylhydrazones are few [12–18].
mixture was refluxed for 3 h. A precipitate that formed
was filtered off, washed with ethanol and water, dried
in vacuo at ambient temperature, and recrystallized
from butanol. The yield of H2L was 1.13 g (55%),
mp = 191°C.
Here we report the results of the synthesis and
structural study of thiobenzoylhydrazone 2ꢀ(Nꢀtosylꢀ
amino)benzaldehyde (H2L), the product of its oxidaꢀ
tion (HL'), and the H2Lꢀbased Cu(II) and Zn(II)
complexes, [Cu(L)(DMF)] (
II), as well as the Xꢀray diffraction analysis results of
compounds HL' and
I) and [ZnL(CH3OH)]
(
For C21H19N3O2S2
I.
anal. calcd., %: C, 61.59;
Found, %: C, 61.85;
H, 4.68;
H, 4.62;
N, 10.26.
N, 10.39.
EXPERIMENTAL
, cm–1): 3393, 3273
ν
(NH), 1606
ν
(C=N), 1276
Commercially available thiobenzhydrazide was
used for the synthesis of H2L. NꢀTosylaminobenzaldeꢀ
hyde was synthesized by a described procedure [19].
Solvents were purified and dried using standard proceꢀ
dures [20].
IR spectra were recorded on a Varian Scimitar 1000
FTꢀIR instrument in the range from 400 to 4000 cm–1
(suspensions in Nujol). 1H NMR spectra were
IR
(
ν
νas(SO2), 1157 νs(SO2), 1355, 840 ν(C=S).
Synthesis of compound HL' was carried out by the
slow crystallization of thiobenzoylhydrazone Н2L
from a DMF solution in the presence of air oxygen.
For C21H17N3O2S2
detected in deuterated dimethyl sulfoxide (DMSOꢀd6
)
anal. calcd., %: C, 61.90;
Found, %: C, 62.07;
H, 4.20;
H, 4.12;
N, 10.31.
N, 10.44.
on a Varian Unity 300 spectrometer (300 MHz) in the
Fourier impulse mode using hexamethyldisilane as an
internal standard. Elemental analysis was carried out
367

368
POPOV et al.
, cm–1): 3317
ν
(NH), 1600
ν
(C=N), 1278
Bruker APEX II diffractometers (Mo
K
,
λ
=
IR (
ν
α
1
0.71073 Å, graphite monochromator) at 120 and
100 K, respectively. The initial array of the measured
intensities was processed using the SAINT [21] and
νas(SO2), 1155 νs(SO2). H NMR (DMSOꢀd6),
ppm: 12.84 s (1H, NH), 7.98 d (2H, = 7.8 Hz,
CHarom), 7.70 d (2H, = 7.6 Hz, CHarom), 7.5 m
(6H, CHarom), 7.23 d (1H, = 7.5 Hz, CHarom), 6.8 m
δ
,
J
J
SADABS [22] programs. The structures of HL' and
I
J
were solved by a direct method and refined by fullꢀ
matrix least squares in the anisotropic approximation
for nonꢀhydrogen atoms for F2. All calculations were
performed using the SHELXTL program package
[23]. The experimental characteristics and crystalloꢀ
(2H, CHarom), 2.45 s (3H, CH3).
Synthesis of I. A solution of copper(II) acetate
(1 mmol) in hot methanol (20 mL) was added to a hot
solution of H2L (1 mmol) in methanol (10 mL). The
reaction mixture was refluxed for 5 h. A brown precipꢀ
itate was filtered off, washed with methanol, and
recrystallized from DMF. The yield of
(59%).
graphic data for HL' and
I are given in Table 1.
Selected interatomic distances and bond angles are
listed in Table 2. The coordinates of atoms and temꢀ
perature factors were deposited with the Cambridge
Crystallographic Data Centre (nos. 794877 (HL') and
I was 0.32 g
For C24H24N4O3S2Cu
794882 (I); deposit@ccdc.cam.ac.uk or http://www.
anal. calcd., %: C, 52.98; H, 4.45; N, 10.30; Cu, 11.68. ccdc.cam.ac.uk/data_request/cif).
Found, %: C, 53.06; H, 4.32; N, 10.47; Cu, 11.59.
IR (
νs(SO2).
ν
, cm–1): 1602
(C=N), 1264 νas(SO2), 1136
ν
RESULTS AND DISCUSSION
The structure of thiobenzoylhydrazone H2L was
determined by IR and H NMR spectroscopy. Comꢀ
Synthesis of II. A solution of zinc(II) acetate
(1 mmol) in methanol (10 mL) was added to a hot
solution of H2L (1 mmol) in methanol (10 mL). The
reaction mixture was refluxed for 1 h. A yellow precipꢀ
itate was filtered off, washed with methanol, and dried
in vacuo at ambient temperature. The yield of II was
0.35 g (70%).
1
pound H2L can exist as three tautomeric forms H2Lа–c
[24–26] (see the scheme). The character of the
1H NMR spectrum of compound H2L in DMSOꢀd6
indicates that the solution contains two tautomeric
forms: the open thiobenzoylhydrazone form H2La and
the cyclic 4ꢀmethylꢀNꢀ(2ꢀ(5ꢀphenylꢀ2,3ꢀdihydroꢀ
1,3,4ꢀthiadiazolylꢀ2)phenyl)benzoic form H2Lc in a
molar ratio of ~2 : 1. The singlets from the NH protons
of the tosylamine and hydrazide fragments at 11.4 and
9.8 ppm, respectively, and the singlet from the azomeꢀ
thine proton at 8.7 ppm were assigned to the open
form of H2La. Upon cyclization the signals from the
NH protons of the tosylamine and thiadiazole fragꢀ
ments are shifted to 13.12 and 8.4 ppm, respectively.
The signal at 6.8 ppm was attributed to the CH proton
of the thiadiazole ring. The positions of signals from
the protons of the methyl groups for the open and
cyclic forms also differ, being at 2.34 and 2.41 ppm,
respectively. The signals from the protons of the NH
groups disappear upon the addition of D2O, which
For C22H21N3O3S2Zn
anal. calcd., %: C, 52.33;
Found, %: C, 52.6;
H, 4.19;
H, 4.05;
N, 8.32.
N, 8.49.
IR (
ν
, cm–1): 3350
ν
(OH), 1600
ν
(C=N), 1267
νas(SO2), 1140 νs(SO2). 1H NMR (DMSOꢀd6),
δ
, ppm:
8.74 s (1H, CHN), 8.15 m (2H, CHarom), 7.67 d (2H,
J
J
= 8.4 Hz, CHarom), 7.48 m (4H, CHarom), 7.33 d (1H,
= 7.8 Hz, CHarom), 7.26 m (3H, CHarom), 6.95 t
(2H,
J
= 8.1 Hz, CHarom), 4.09 m (1H,
J
= 5.4 Hz,
OHmethanol), 3.16 d (3H,
CH3).
J = 5.4 Hz, CH3), 2.28 s (3H,
Xꢀray diffraction analyses of compounds HL' and
I
were carried out on Bruker SMART 1000 CCD and indicates the acidic character of these protons.
Ts
NH
Ts
NH
Ts
NH
Ts
NH
H
[O]
N
N
N
N
N
N
S
H
N
S
S
HN
HS
Ph
Ph
Ph
Ph
H2La
H2Lb
H2Lc
HL'
Scheme.
Cyclic form H2Lc undergoes irreversible oxidation Single crystals of the oxidation product (HL'), the
by air oxygen to form the 1,3,4ꢀthiadiazole derivative. structure of which was determined by Xꢀray diffraction
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2ꢀ(NꢀTOSYLAMINO)BENZALDEHYDE THIOBENZOYLHYDRAZONE
369
Table 1. Crystallographic data and experimental and refinement details for compounds HL' and
I
Value
Parameter
HL'
I
Formula weight
Crystal size, mm
Temperature, K
Crystal system
407.50
0.40 × 0.20 × 0.15
120(2)
544.13
0.50 × 0.35 × 0.25
100(2)
Triclinic
Monoclinic
Space group
C2/c
P
1
a
, Å
, Å
9.287(2)
9.798(2)
10.779(3)
88.693(5)
77.669(5)
78.257(5)
937.9(4)
2
25.052(2)
7.5146(7)
26.017(2)
90
b
c
, Å
, deg
, deg
, deg
α
β
99.630(2)
90
γ
V
Z
, Å3
4828.7(8)
8
ρcalcd, g/cm3
, mm–1
(000)
θmax, deg
1.443
1.497
1.112
2248
μ
0.307
F
424
2
56
56
Number of measured reflections
Number of independent reflections
9564
25750
5794
4483
Number of reflections with
I
> 2σ(I
)
2569
4223
Ranges of reflection indices
–12 <
–12 <
–14 <
258
h
k
l
< 12,
< 12,
< 14
–32 <
–9 <
–34 <
h
k
l
< 32,
< 9,
< 34
Number of refined parameters
R1 > 2 ))
310
(I
σ(
I
0.0520
0.1046
0.0388
0.0900
wR2 (all reflections)
Goodnessꢀofꢀfit (all reflections)
1.005
1.008
Δρmax
/
Δρmin
,
e
Å–3
0.446/–0.502
0.506/–0.489
analysis (Fig. 1), were obtained by the slow crystallizaꢀ coplanar and the S(1)–O(1) bond (1.436 Å) is someꢀ
what longer than S(1)–O(2) (1.428 Å).
tion of hydrazone H2L from DMSO.
The reaction of thiobenzoylhydrazone H2L with
copper(II) acetate afforded complex I. The absence in
The thiadiazole cycle in an HL' molecule is nearly
coplanar to the benzene ring of the benzaldehyde fragꢀ
ment, and the rotation angle with respect to the
its IR spectrum of absorption bands of the NH groups
of the tosylamine and hydrazone fragments and
C(2)⎯C(3) bond is 3.60(13)°. The second benzene
ν
(C=S) and the shift of the absorption band (С=N)
ν
ring is turned with respect to the thiadiazole cycle
around the C(1)–C(9) bond by 26.10(13)°. The N(2)
atom is joined by an intramolecular hydrogen bond
with the tosylamine group (N(1)–H(1N1) 0.81(2),
to the lowꢀfrequency region indicate the coordination
of the L2– ligand in the doubly deprotonated thiol
form. The lowꢀfrequency shift of absorption bands of
stretching vibrations of the SO2 group indicates a posꢀ
sible participation of the oxygen atom of the tosyl fragꢀ
ment in coordination.
N(1)⋅⋅⋅N(2) 1.99(2), and N(1)⋅⋅⋅N(2) 2.652(3) Å
N(1)H(1N1)N(2) 139(2) ). The tosyl group is turned
out with respect to the S(1)–N(1) bond in such a way
that the S(1)=O(1) and N(1)–H(1N1) bonds are being 1.88 µB at 293 K, remains almost unchanged
,
°
The effective magnetic moment of complex I,
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 39
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370
POPOV et al.
Table 2. Selected interatomic distances and bond angles in
the structures of compounds HL' and
The structure of complex
I with the composition
I
[Cu(L)(DMF)] was determined by Xꢀray diffraction
analysis (Fig. 2). Hydrazone H2L is coordinated in the
doubly deprotonated thiol form, which is confirmed
by the pronounced conjugation of ordinary and douꢀ
ble bonds in the chain of atoms C(8)=N(3)–
N(2)=C(7)–C(6) and the correspondence of the
C(8)–S(1) interatomic distance (1.748(2) Å) to the
carbon–sulfur ordinary bond.
Bond
d
, Å
Angle
ω
, deg
HL'
S(1)–O(2)
S(1)–O(1)
S(1)–N(1)
S(1)–C(15)
S(2)–C(1)
S(2)–C(2)
N(1)–C(4)
N(2)–C(2)
N(2)–N(3)
N(3)–C(1)
C(1)–C(9)
C(2)–C(3)
1.4278(19) O(2)S(1)C(15) 107.41(12)
1.4359(18) O(1)S(1)C(15) 109.46(11)
1.626(2)
1.758(3)
1.729(3)
1.729(3)
1.398(3)
1.305(3)
1.360(3)
1.303(3)
1.472(4)
1.473(4)
N(1)S(1)C(15) 105.71(12)
C(1)S(2)C(2)
C(4)N(1)S(1)
N(2)C(2)C(3)
N(2)C(2)S(2)
C(3)C(2)S(2)
N(1)C(4)C(5)
N(1)C(4)C(3)
N(3)C(1)C(9)
N(3)C(1)S(2)
I
87.42(13)
127.8(2)
124.3(2)
112.5(2)
123.23(19)
121.8(2)
119.0(2)
123.2(2)
113.6(2)
The coordination polyhedron of the copper atom
can be described as a strongly distorted trigonal bipyrꢀ
amid, whose axial positions are occupied by the S(1)
and N(1) atoms of the L ligand (the S(1)Cu(1)N(1)
angle is 158.13(7) ), while the equatorial positions are
°
occupied by the atoms N(2) of the hydrazone fragꢀ
ment, O(2) of the tosyl group of the ligand L, and O(3)
of the coordinated DMF molecule. The Cu(1)–O(2)
bond is weak (2.6775(18) Å, which is by 0.24 Å shorter
than the sum of the van der Waals radii of Cu and O)
[28]. The coordination of the O(2) atom to the copper
atom is confirmed by a significant distortion of the
coordination polyhedron and an almost planar strucꢀ
ture of the fourꢀmembered chelate cycle
Cu(1)N(1)S(2)O(2) (the maximum deviation of the
atoms from the rootꢀmeanꢀsquare plane of the cycle is
Cu(1)–S(1)
2.2116(7) N(1)Cu(1)N(2) 92.54(8)
Cu(1)–N(1) 1.9419(19) N(1)Cu(1)O(3) 96.64(8)
Cu(1)–N(2) 1.9421(19) N(2)Cu(1)O(3) 139.78(8)
Cu(1)–O(3) 1.9891(17) N(1)Cu(1)S(1) 158.14(6)
≤
0.027 Å).
Cu(1)–O(2) 2.677(3)
N(2)Cu(1)S(1)
O(3)Cu(1)S(1)
86.85(6)
97.88(5)
The fiveꢀ and sixꢀmembered chelates in a molecule
of complex I are nonplanar. The former has an enveꢀ
lope conformation, and the Cu(1) atom serving as a
“flap” deviates from the mean plane of other four
atoms by 0.2219(3) Å. The sixꢀmembered chelate has
an asymmetrical sofa conformation: the N(1), C(1),
C(6), and C(7) atoms lie in one plane, whereas the
N(2) and Cu(1) atoms are shifted with respect to this
plane by 0.144(2) and 0.5322(3) Å, respectively. The
hydrogen atoms of the methyl group of the tosyl fragꢀ
ment are disordered over two equally populated posiꢀ
tions, each of which corresponds to the turn of the
N(1)Cu(1)O(2) 60.56(8)
N(2)Cu(1)O(2) 135.76(7)
O(3)Cu(1)O(2)
81.43(6)
S(1)Cu(1)O(2) 105.70(4)
(1.82 µB) on cooling to the boiling point of liquid
nitrogen, which indicates the absence of an intermoꢀ
lecular exchange interaction between the copper(II)
ions [27].
methyl group by 60
°
around the C(18)–C(21) bond.
O(1)
C(19)
C(20)
C(18)
C(11)
C(10)
C(21)
N(3)
S(2)
S(1)
C(9)
N(2)
C(12)
C(13)
C(15)
C(16)
C(17)
N(1)
C(4)
O(2)
C(1)
C(2)
C(14)
C(3)
C(5)
C(6)
C(8)
C(7)
Fig. 1. Structure of compound HL' in the representation of atoms by thermal displacement ellipsoids with the 50% probability.
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 39 No. 5 2013

2ꢀ(NꢀTOSYLAMINO)BENZALDEHYDE THIOBENZOYLHYDRAZONE
371
C(23)
N(4)
C(24)
C(11)
C(10)
C(22)
S(1)
O(3)
O(2)
C(12)
C(13)
C(19)
C(9)
C(8)
N(3)
C(21)
C(18)
C(20)
C(15)
Cu(1)
C(17)
C(16)
C(14)
S(2)
O(1)
N(1)
C(1)
N(2)
C(7)
C(6)
C(2)
C(3)
C(5)
C(4)
Fig. 2. Structure of complex I in the representation of atoms by thermal displacement ellipsoids with the 50% probability.
6. Padhye, S. and Kauffman, G.B., Coord. Chem. Rev.
1985, vol. 63, no. 1, p. 127.
,
Complex II with the composition [ZnL(CH3OH)
]
was obtained by the reaction of thiobenzoylhydrazone
H2L with zinc(II) acetate. Its IR spectrum is similar to
7. West, D.X. and Liberta, A.E., Coord. Chem. Rev., 1993,
vol. 123, nos. 1–2, p. 49.
that for complex
I and indicates the coordination of
the ligand in the doubly deprotonated thiol form and
the possible participation in the coordination of the
oxygen atom of the tosyl fragment. The broad band at
3350 cm–1 was assigned to vibrations of the OH group
of the coordinated methanol molecule. The 1H NMR
spectrum of the complex in DMSOꢀd6 contains sigꢀ
nals from the protons of CH3OH, whose intensities
exactly correspond to one methanol molecule per L2–
anion [29]. These data suggest that the zinc(II) comꢀ
plex has a structure similar to that of the copper(I)
complex, and the distinction is the coordination to the
metal of the methanol molecule instead of the DMF
molecule.
8. Casas, J.S., GarciaꢀTasende, M.S., and Sordo, J.,
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2013