Synthesis, Characterization and Crystal Structures of Oxidovanadium(V) and Dioxidomolybdenum(VI) Complexes Derived from 2-bromo-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide with Catalytic Property

Article abstract of DOI:10.1134/S1070328419110034

Abstract: A hydrazone compound 2-bromo-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (H₂L) was prepared and characterized by IR, UV-Vis and NMR spectra. Based on the hydrazone compound, a new oxidovanadium(V) and a new dioxidomolybdenum(VI) complexes, [VO(L)(OEt)(EtOH)] (I) and [MoO₂(L)(OH₂)] (II), were prepared and characterized by IR, UV-Vis, NMR spectra, and single crystal X-ray diffraction (CIF files nos. 1866755 (I) and 1866756 (II)). Complex I crystallizes as the monoclinic space group P2₁/c with unit cell dimensions a = 12.8733(12), b = 13.5088(13), c = 11.9262(11) ?, β = 91.765(2)°, V = 2073.0(3) ?³, Z = 4, R₁ = 0.0524, wR₂ = 0.1329, GOOF = 1.245. Complex II crystallizes as the monoclinic space group P2₁/c with unit cell dimensions a = 8.1140(9), b = 16.2975(19), c = 13.4318(15) ?, β = 106.456(2)°, V = 1703.4(3) ?³, Z = 4, R₁ = 0.0296, wR₂ = 0.0728, GOOF = 1.046. X-ray analysis indicates that the complexes are mononuclear species with the metal atoms in octahedral coordination. The complexes were studied for catalytic oxidation property on some olefins with tert-butyl hydrogen peroxide as oxidant.

Full text of DOI:10.1134/S1070328419110034

ISSN 1070-3284, Russian Journal of Coordination Chemistry, 2019, Vol. 45, No. 11, pp. 809–816. © Pleiades Publishing, Ltd., 2019.
Synthesis, Characterization and Crystal Structures
of Oxidovanadium(V) and Dioxidomolybdenum(VI) Complexes
Derived from 2-Bromo-N'-(2-Hydroxy-3-
Methoxybenzylidene)benzohydrazide with Catalytic Property
H. Y. Liua, b, *, X. L. Zoua, b, H. H. Yanga, b, Y. F. Yea, b, and L. J. Yanga, b
aSchool of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan, 528453 P.R. China
bGuangdong Cosmetics Engineering and Technology Research Center, Zhongshan, 528453 P.R. China
*e-mail: liuhuanyu03@163.com
Received September 27, 2018; revised April 10, 2019; accepted May 15, 2019
Abstract—A hydrazone compound 2-bromo-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (H2L)
was prepared and characterized by IR, UV-Vis and NMR spectra. Based on the hydrazone compound, a new
oxidovanadium(V) and
a
new dioxidomolybdenum(VI) complexes, [VO(L)(OEt)(EtOH)] (I)
and [MoO2(L)(OH2)] (II), were prepared and characterized by IR, UV-Vis, NMR spectra, and single crystal
X-ray diffraction (CIF files nos. 1866755 (I) and 1866756 (II)). Complex I crystallizes as the monoclinic
space group P21/c with unit cell dimensions a = 12.8733(12), b = 13.5088(13), c = 11.9262(11) Å, β =
91.765(2)°, V = 2073.0(3) Å3, Z = 4, R1 = 0.0524, wR2 = 0.1329, GOOF = 1.245. Complex II crystallizes as the
monoclinic space group P21/c with unit cell dimensions a = 8.1140(9), b = 16.2975(19), c = 13.4318(15) Å,
β = 106.456(2)°, V = 1703.4(3) Å3, Z = 4, R1 = 0.0296, wR2 = 0.0728, GOOF = 1.046. X-ray analysis indi-
cates that the complexes are mononuclear species with the metal atoms in octahedral coordination. The com-
plexes were studied for catalytic oxidation property on some olefins with tert-butyl hydrogen peroxide as oxi-
dant.
Keywords: hydrazone, vanadium complex, molybdenum complex, crystal structure, catalytic property
DOI: 10.1134/S1070328419110034
INTRODUCTION
H
In recent years, study on the oxidation of olefins
has received particular attention in material chemistry.
High-valent vanadium and molybdenum complexes
have attracted continuing interest due to their import-
ant practical applications as catalysts in the ammoxi-
dation of propene, the sulfoxidation and epoxidation
of olefins, etc. [1–7]. The ability of vanadium and
molybdenum to form stable complexes with oxygen-
and nitrogen-containing ligands led to the develop-
ment of vanadium and molybdenum Schiff base com-
plexes which are efficient catalysts both in homoge-
N
N
O
Br
OH
OMe
(H2L)
EXPERIMENTAL
Materials and methods. VO(Acac)2 and MoO2-
neous and heterogeneous reactions [8–13]. Recently, (Acac)2 and organic materials were purchased from
we have reported some metal complexes with Schiff
bases, and their biological aplications [14–16], as well
as catalytic properties [17, 18]. In this paper, as a con-
tinuation of the work on the exploration of new cata-
lytic materials based on vanadium and molybdenum
complexes, a new oxidovanadium(V) and dioxidomo-
lybdenum(VI) complexes, [VO(L)(OEt)(EtOH)] (I)
and [MoO2(L)(OH2)] (II), derived from hydrazone
compound 2-bromo-N'-(2-hydroxy-3-methoxyben-
zylidene)benzohydrazide (H2L) were prepared.
Sigma-Aldrich and used as received. All other reagents
were of analytical reagent grade. Elemental analyses of
C, H and N were carried out in a Perkin-Elmer auto-
mated model 2400 Series II CHNS/O analyzer. FT-
IR spectra were obtained on a Perkin-Elmer 377 FT-
IR spectrometer with samples prepared as KBr pellets.
UV-Vis spectra were obtained on a Lambda 900 spec-
trometer. X-ray diffraction was carried out on a Bruker
APEX II CCD diffractometer. 1H and 13C NMR spec-
tra were recorded on a Bruker FT-NMR 300 MHz
809

810
LIU et al.
spectrometer using (CD3)2SO as solvent. Gas chroma- suitable for X-ray diffraction, were grown from the
solution upon slowly evaporation within a few days.
The crystals were isolated by filtration, washed with
ethanol and dried in vacuum containing anhydrous
CaCl2.
tography (GC) analyses were performed on a Shi-
madzu GC-2010 gas chromatograph.
Synthesis of the hydrazone H2L. The ethanolic
solution (20 mL) of 3-methoxysalicylaldehyde
(0.01 mol, 1.52 g) was added to the ethanolic solution
(30 mL) of 2-bromobenzohydrazide (0.01 mol, 2.12 g)
with stirring. The mixture was stirred for 30 min at
room temperature and left to slowly evaporate to give
colorless crystalline product, which were recrystal-
lized from ethanol and dried in vacuum containing
anhydrous CaCl2.
For C15H13N2O6BrMo
Anal. calcd., %
Found, %
C, 36.54
C, 36.72
H, 2.66
H, 2.77
N, 5.68
N, 5.56
The yield was 63%. IR (KBr; νmax, cm–1): 3361, 3283 w
ν(OH), 1598 s ν(C=N), 1446 m ν(C=C), 1355 s
ν(Ar–O), 1158 s ν(C–O), 948 s, 862 s ν(Mo=O). UV-
Vis data (EtOH; λmax, nm): 220, 290. 1H NMR
For C15H13N2O3Br (H2L)
Anal. calcd., %
Found, %
C, 51.60
C, 51.45
H, 3.75
H, 3.83
N, 8.02
N, 8.13
(300 MHz, d6-DMSO; δ, ppm): 8.91 (s., 1H,
CH=N), 7.76–7.71 (m., 2H, ArH), 7.51–7.43 (m.,
2H, ArH), 7.32–7.25 (q., 2H, ArH), 7.03 (t., 1H,
ArH), 3.82 (s., 3H, OCH3).
The yield was 87%. IR (KBr; νmax, cm–1): 3443 w
ν(OH), 3335 w ν(NH), 1651 s ν(C=O), 1602 w
ν(C=N), 1521 m ν(Ar–O), 1288 m ν(C–O). UV-Vis
X-ray crystallography. X-ray diffraction was carried
out at a Bruker APEX II CCD area diffractometer
equipped with MoKα radiation (λ = 0.71073 Å). The
collected data were reduced with SAINT [19], and
multi-scan absorption correction was performed using
SADABS [20]. The structures of the complexes were
solved by direct method, and refined against F 2 by
full-matrix least-squares method using SHELXTL
[21]. All of the non-hydrogen atoms were refined
anisotropically. The ethanol hydrogen atom in I and
the water hydrogen in II were located from electronic
density maps and refined isotropically. The remaining
1
data (EtOH; λmax, nm): 221, 292, 333. H NMR
(300 MHz, d6-DMSO; δ, ppm): 12.47 (s., 1H, OH),
11.18 (s., 1H, NH), 8.85 (s., 1H, CH=N), 8.73 (d., 1H,
ArH), 8.15 (d., 1H, ArH), 8.07 (d., 1H, ArH), 7.67
(m., 1H, ArH), 7.08–7.03 (m., 2H, ArH), 6.87 (t., 1H,
ArH), 3.82 (m., 3H, OCH3).
Synthesis of complex I. The hydrazone compound
H2L (0.1 mmol, 34.8 mg) and VO(Acac)2 (0.1 mmol,
26.5 mg) were mixed in ethanol (20 mL). The mixture
was refluxed for 1 h and then cooled to room tempera-
ture. Single crystals of the complex, suitable for X-ray
diffraction, were grown from the solution upon slowly hydrogen atoms were placed in calculated positions
evaporation within a few days. The crystals were iso-
lated by filtration, washed with ethanol and dried in
vacuum containing anhydrous CaCl2.
and constrained to ride on their parent atoms. The
crystallographic data and refinement parameters for
the compounds are listed in Table 1. Selected bond
lengths and angles are listed in Table 2.
For C19H22N2O6BrV
The supplementary crystallographic data for I and
II have been deposited with the Cambridge Crystallo-
graphic Data Centre (CCDC nos. 1866755 and
1866756, respectively; deposit@ccdc.cam.ac.uk or
http://www.ccdc.ac.uk/conts/retrieving.html).
Anal. calcd., % C, 45.17; H, 4.39;
Found, %: C, 44.96; H, 4.51;
N, 5.54.
N, 5.63.
The yield was 45%. IR (KBr; νmax, cm–1): 3423 w
ν(OH), 1607 s ν(C=N), 1446 m ν(C=C), 1349 m
ν(Ar–O), 1095 m ν(C–O), 980 s ν(V=O). UV-Vis
Catalytic oxidation experiment. Catalytic experi-
ment was carried out in a 50 mL glass round-bottom
flask fitted with a reflux condenser and placed in an oil
bath at 353(2) K under continuous stirring. The cata-
lytic oxidation experiment was carried out as follows:
molybdenum(VI) complex (0.032 mmol) was dis-
solved in 10 mL 1,2-dichloroethane. Then 10 mmol
alkene was added to the reaction mixture and 30 mmol
TBHP (tert-butyl hydroperoxide) was added. The
reaction mixture was refluxed for 1 h. The reaction
1
data (EtOH; λmax, nm): 220, 306, 453. H NMR
(300 MHz, d6-DMSO; δ, ppm): 8.86 (s., 1H,
CH=N), 7.78–7.74 (m., 2H, ArH), 7.49 (t, 1H, ArH),
7.42 (t, 1H, ArH), 7.30 (d, 1H, ArH), 7.18 (d, 1H,
ArH), 6.92 (t, 1H, ArH), 5.68–5.56 (q., 2H, CH2),
3.85 (s., 3H, OCH3), 3.47–3.43 (q., 2H, CH2), 1.51
(t., 3H, CH3), 1.06 (t., 3H, CH3).
Synthesis of complex II. The hydrazone compound
H2L (0.1 mmol, 34.8 mg) and MoO2(Acac)2 products were monitored at periodic time intervals
using gas chromatography. The oxidation products
were identified by comparison with authentic samples
(0.1 mmol, 32.6 mg) were mixed in ethanol (20 mL).
The mixture was refluxed for 1 h and then cooled to
room temperature. Single crystals of the complex, (retention times in GC).
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SYNTHESIS, CHARACTERIZATION AND CRYSTAL STRUCTURES
Table 1. Crystallographic data and structure refinement for I and II
811
Value
Parameter
I
II
Formula weight
Crystal shape/color
T, K
505.24
Block/yellow
298(2)
493.12
Block/brown
298(2)
Crystal dimensions, mm
0.20 × 0.18 × 0.18
Monoclinic
P21/c
0.31 × 0.27 × 0.23
Monoclinic
P21/c
Crystal system
Space group
a, Å
b, Å
c, Å
12.8733(12)
13.5088(13)
11.9262(11)
91.765(2)
8.1140(9)
16.2975(19)
13.4318(15)
106.456(2)
1703.4(3)
β, deg
V, Å3
2073.0(3)
Z
4
4
calcd, g cm–3
1.619
1.923
ρ
μ(MoKα), mm–1
2.444
3.150
F(000)
1024
968
Measured reflections
Unique reflections
Observed reflections (I ≥ 2σ(I))
Min and max transmission
Parameters
12100
3865
2772
0.6406 and 0.6674
9891
3167
2603
0.4322 and 0.4834
262
3
233
3
Restraints
Goodness of fit on F2
1.245
1.046
R1, wR2 (I ≥ 2σ(I))*
0.0524, 0.1329
0.0763, 0.1450
0.0296, 0.0728
0.0425, 0.0781
R1, wR2 (all data)*
2
2
2 1/2
* R = F – F /F , wR = [∑ w(
–
2)/∑ w( ) ]
.
Fo Fc
Fo
1
o
c
o
2
RESULTS AND DISCUSSION
pared by the reaction of the hydrazone compound with
VO(Acac)2 and MoO2(Acac)2 in ethanol, respectively
(Scheme 2), followed by recrystallization. Elemental
analyses of the compounds are in accordance with the
The hydrazone compound H2L was readily prepared
by the condensation reaction of a 1 : 1 molar ratio of
2-bromobenzohydrazide with 3-methoxysalicylaldehyde
in ethanol (Scheme 1). Complexes I and II were pre- molecular structures proposed by the X-ray analysis.
H
N
O
H
N
N
+
O
Br
H2N
OH
OH
O
Br
OMe
OMe
Scheme 1.
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LIU et al.
Table 2. Selected bond distances (Å) and angles (deg) for complexes I and II
Bond
d, Å
Bond
d, Å
I
V(1)–O(1)
V(1)–O(3)
V(1)–O(4)
1.850(3)
1.583(3)
2.374(3)
V(1)–O(2)
V(1)–O(5)
V(1)–N(1)
1.949(3)
1.772(3)
2.128(3)
II
Mo(1)–O(1)
Mo(1)–O(4)
Mo(1)–O(5)
1.908(2)
1.687(2)
2.301(2)
Mo(1)–O(2)
Mo(1)–O(3)
Mo(1)–N(1)
2.017(2)
1.711(2)
2.236(3)
Angle
ω, deg
Angle
ω, deg
I
O(3)V(1)O(5)
O(5)V(1)O(1)
O(5)V(1)O(2)
O(3)V(1)N(1)
O(1)V(1)N(1)
O(3)V(1)O(4)
O(1)V(1)O(4)
N(1)V(1)O(4)
102.21(17)
103.56(14)
93.86(14)
91.93(16)
82.83(13)
175.51(16)
76.92(12)
84.68(13)
O(3)V(1)O(1)
O(3)V(1)O(2)
O(1)V(1)O(2)
O(5)V(1)N(1)
O(2)V(1)N(1)
O(5)V(1)O(4)
O(2)V(1)O(4)
99.75(17)
102.19(16)
148.30(14)
163.08(16)
73.88(13)
81.62(14)
79.74(12)
II
O(4)Mo(1)O(3)
O(3)Mo(1)O(1)
O(3)Mo(1)O(2)
O(4)Mo(1)N(1)
O(1)Mo(1)N(1)
O(5)Mo(1)O(4)
O(1)Mo(1)O(5)
N(1)Mo(1)O(5)
106.44(12)
105.17(11)
95.99(11)
92.91(11)
81.02(10)
168.98(11)
79.63(11)
76.08(9)
O(4)Mo(1)O(1)
O(4)Mo(1)O(2)
O(1)Mo(1)O(2)
O(3)Mo(1)N(1)
O(2)Mo(1)N(1)
O(3)Mo(1)O(5)
O(2)Mo(1)O(5)
98.24(12)
97.55(12)
148.68(11)
158.31(11)
71.31(10)
84.51(10)
79.72(10)
N
N
O
O
Br
H2L + VO(acac)2
O
V
OMe
EtOH
N
OEt
N
O
O
Br
H2L + MoO2(acac)2
O
Mo
OMe
Scheme 2.
O
OH2
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SYNTHESIS, CHARACTERIZATION AND CRYSTAL STRUCTURES
Table 3. Geometric parameters of hydrogen bonds for complexes I and II*
813
Distance, Å
H∙∙∙A
D−H∙∙∙A
Angle D−H∙∙∙A, deg
D−H
D∙∙∙A
I
O(4)−H(4)∙∙∙N(2)i
0.85(1)
0.85(1)
2.22(3)
2.958(4)
146(5)
II
O(5)−H(5B)∙∙∙O(3)ii
1.92(2)
2.741(3)
2.774(4)
165(4)
167(4)
O(5)−H(5A)∙∙∙N(2)iii
0.85(1)
1.94(2)
i
ii
iii
* Symmetry codes: x, 3/2 – y, –1/2 + z; 1 – x, 1 – y, 1 – z; –x, 1 – y, 1 – z.
In the spectra of the hydrazone compound and the geometry around the metal atoms can be described as
complexes, the weak and broad bands in the region distorted octahedral with the tridentate hydrazone
3450–3280 cm–1 are assigned to the vibration of O–H
bonds. The weak and sharp band located at 3335 cm–1
of the hydrazone compound is assigned to the vibra-
tion of N–H bond. The position of the bands demon-
strates that the N–H hydrazone protons are engaged
in hydrogen bonding. The intense bands at 1651 cm–1
of the hydrazone compound is generated by ν(C=O)
vibration, whereas the band at 1602 cm–1 by the
ν(C=N) one. The non-observation of the ν(C=O)
bands, that present in the spectra of the hydrazone
compound, indicates the enolization of the amide
functionality upon coordination to the V- and Mo-
centers. Instead strong bands at 1607 cm–1 for I and
1598 cm–1 for II are observed, which can be attributed
to the asymmetric stretching vibration of the conju-
gated CH=N–N=C–O groups, characteristic for the
coordination of the enolate form of the compounds.
The bands at 980 cm–1 for I is assigned to ν(V=O)
[22], and the bands at 948 and 862 cm–1 for II is
assigned to ν(Mo=O) [23].
ligands coordinated in a meridional fashion, forming
five- and six-membered chelate rings with bite angles
of 73.88(13)° and 82.83(13)° (I), and 71.31(10)° and
81.02(10)° (II), respectively, typical for this type of
ligand systems [24]. In complex I, one ethanolato
ligand lies trans to the hydrazone imino N atom. One
ethanol O atom trans to the oxo group completes the
distorted octahedral coordination sphere at a rather
elongated distance of 2.374(3) Å due to the trans influ-
ence of the oxo group. In complex II, one oxo group
(O(3)) lies trans to the hydrazone imino N atom. One
water O atom trans to the other oxo group (O(4)) com-
pletes the distorted octahedral coordination sphere at
a rather elongated distance of 2.301(2) Å due to the
trans influence of the oxo group. As expected, the
hydrazone compounds in both complexes coordinate
in their doubly deprotonated enolate form which is
consistent with the observed O(2)–C(9) and N(2)–
C(9) bond lengths of 1.298(5) and 1.296(5) Å in I, and
1.300(4) and 1.310(4) Å in II, respectively. This agrees
with reported vanadium or molybdenum complexes
containing the enolate form of this ligand type [25–
28]. The dihedral angles between the two benzene
rings of the hydrazone ligands are 73.6(4)° for I and
7.6(5)° for II.
In the electronic spectra of the complexes, the low-
est energy transition band is observed at 453 nm for I,
while no such band for II, which is attributed to
LMCT transition as charge transfer from p-orbital
on the lone-pair of ligands’ oxygen atoms to the empty
d-orbital of the vanadium atom. The other strong
bands in the range of 280–320 nm and at about
220 nm in the spectra of both complexes are similar to
In the crystal packing structure of complex I, the
complex molecules are linked by ethanol molecules
through intermolecular hydrogen bonds of O–H···N
(Table 3), leading to the formation of one-dimen-
the absorption band in the spectrum of the hydrazone sional chains along the z-axis direction (Fig. 2a). In
the crystal packing structure of complex II, the com-
plex molecules are linked by water molecules through
intermolecular hydrogen bonds of O–H···O and O–
H···N (Table 3), leading to the formation of dimers
compound, so they are attributed to the intra-ligand π
→ π* absorption peak of the ligands.
Molecular structures of complexes I and II are
shown in Fig. 1. In both complexes, the coordination (Fig. 2b).
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 45 No. 11 2019

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LIU et al.
(a)
C(5)
C(8)
C(6)
C(4)
C(3)
C(11)
C(12)
C(10)
N(2)
C(9)
N(1)
O(3)
C(13)
C(2)
C(1)
O(1)
C(14)
C(15)
Br(1)
O(2)
V(1)
O(5)
C(16)
O(6)
O(4)
C(7)
C(19)
C(18)
C(17)
(b)
C(4)
C(5)
C(11)
C(3)
C(7)
C(12)
C(8)
N(2)
C(6)
C(10)
C(9)
O(2)
N(1)
C(13)
C(14)
C(2)
O(4)
C(1)
O(1)
C(15)
Mo(1)
O(6)
O(5)
Br(1)
O(3)
Fig. 1. Perspective views of complexes I (a) and II (b) with the atom labeling scheme. Thermal ellipsoids are drawn at the 30%
probability level.
1-Butene, 1-pentene, 4-chloro-1-butene, phenyl- molybdenum(VI) complexes with phloroglucinol and
ene 4-methylphenylene, 3-methylphenylene, 2-meth-
ylphenylene, 4-chlorophenylene, 3-chlorophenylene,
and 2-chlorophenylene were used as the substrates.
The catalytic oxidation results are given in Table 4.
The conversion for both aliphatic and aromatic sub-
strates are 100% for either the vanadium complex or
the molybdenum complex. High epoxide yields (82–
90%) are obtained for aliphatic substrates for the
molybdenum complex, while somewhat lower yields
(73–83%) for the vanadium complex. As for the aro-
matic substrates, the epoxide yields (90–100%) are
higher than the aliphatic substrates for both com-
plexes. The catalytic oxidation property of the molyb-
resorcinol derived ligands [29] and with hydrazone
ligands [30, 31]. The catalytic oxidation property of
the vanadium complex is also similar to those of the
oxidovanadium(V) complexes with hydrazone ligands
[32].
In summary, a new oxidovanadium(V) complex and a
new dioxidomolybdenum(VI) complex were obtained
from the hydrazone ligand 2-bromo-N'-(2-hydroxy-3-
methoxybenzylidene)benzohydrazide. The V and Mo
atoms in the complexes are in octahedral coordination.
The complexes have effective catalytic properties on oxi-
dation of various olefins with tert-butyl hydrogen perox-
denum complex is comparable to those of the dioxido- ide as the oxidant.
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SYNTHESIS, CHARACTERIZATION AND CRYSTAL STRUCTURES
815
Table 4. Details of the catalytic oxidation of olefins catalyzed by the complexes*
Yields, %**
Substrate
Product
I
II
77.5
82.1
O
73.2
82.5
95.8
84.3
89.2
92.6
O
Cl
O
Cl
O
95.0
93.1
94.5
95.3
O
O
O
90.9
93.7
100
100
O
Cl
Cl
100
100
100
100
O
O
Cl
Cl
Cl
Cl
* The molar ratio of catalyst : substrate : TBHP is 1 : 300 : 1000. The reaction was performed in mixture of CH OH–CH Cl (v : v = 3 : 1).
3
2
2
** The yields (%) were measured relative to the starting substrate after 1 h.
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No. 11
2019