N′-(3-bromo-2-hydroxybenzylidene)-4-nitrobenzohydrazide and its oxovanadium(V) complex: Synthesis, crystal structures, and catalytic property

Article abstract of DOI:10.1080/15533174.2012.749907

A new benzohydrazone compound, N′-(3-bromo-2-hydro xybenzylidene)-4-nitrobenzohydrazide (H₂L), and its oxovanadium(V) complex, 2[VOL(BHA)]·CH₃CN, where HBHA is benzohydroxamic acid, was prepared and structurally characterized by physicochemical methods and single-crystal X-ray diffraction. The benzohydrazone compound crystallizes in the monoclinic space group P₂₁/c, with a = 11.2211(15), b = 13.5515(18), c = 9.2850(10) A, β = 90.554(2)°, V = 1411.8(30 A³, Z = 4, R₁ = 0.0757, and wR₂ = 0.1920. The oxovanadium(V) complex crystallizes in the triclinic space group P-1, with a = 11.3754(13), b = 14.7186(19), c = 15.611(2) A, α = 83.952(2)°, β = 72.346(2)°, γ = 69.848(2)°, V = 2338.1(5) A³, Z = 2, R₁ = 0.0886, and wR₂ = 0.2245. X-ray structural analysis indicates that the benzohydrazone ligand coordinates to the V atom through the phenolate O, imino N, and enolic O atoms. The V atom in the complex is coordinated by one benzohydrazone ligand and one BHA ligand, as well as one oxo O atom, forming an octahedral coordination. The crystal structures of the ligand and the complex are stabilized by hydrogen bonds. The complex is an effective catalyst for sulfoxidation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry to view the supplemental file. Copyright Taylor and Francis Group, LLC.

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N′-(3-Bromo-2-Hydroxybenzylidene)-4-
nitrobenzohydrazide and Its Oxovanadium(V) Complex:
Synthesis, Crystal Structures, and Catalytic Property
Ying-Zhen Wang a , Yan Gao a , Yong-Qing Su b , Ping Wang b & Cong Li b
a Department of Chemical Science & Technology , Kunming College , Kunming , P. R. China
b Faculty of Chemistry & Chemical Engineering , Yunnan Normal University , Kunming , P. R.
China
Published online: 13 Mar 2013.
To cite this article: Ying-Zhen Wang , Yan Gao , Yong-Qing Su , Ping Wang & Cong Li (2013) N′-(3-Bromo-2-
Hydroxybenzylidene)-4-nitrobenzohydrazide and Its Oxovanadium(V) Complex: Synthesis, Crystal Structures, and
Catalytic Property, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 43:6, 677-681, DOI:
10.1080/15533174.2012.749907
To link to this article: http://dx.doi.org/10.1080/15533174.2012.749907
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 43:677–681, 2013
Copyright ꢀ Taylor & Francis Group, LLC
C
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2012.749907
Nꢀ-(3-Bromo-2-Hydroxybenzylidene)-4-
nitrobenzohydrazide and Its Oxovanadium(V) Complex:
Synthesis, Crystal Structures, and Catalytic Property
Ying-Zhen Wang,1 Yan Gao,1 Yong-Qing Su,2 Ping Wang,2 and Cong Li2
1Department of Chemical Science & Technology, Kunming College, Kunming, P. R. China
2Faculty of Chemistry & Chemical Engineering, Yunnan Normal University, Kunming, P. R. China
are widely used as drug intermediates in pharmaceutical indus-
A
new benzohydrazone compound, Nꢀ-(3-bromo-2-hydro
tries, and also sulfinyl groups have been used as auxiliaries in a
variety of highly diastereoselective carbon-carbon bond forming
reactions, including the synthesis of α-branched amines, α- and
β-amino acids, aziridines, and amino phosphonic acids.[8,9] Sul-
foxidation catalyzed by complexes of transition metals such as
titanium, manganese, iron, molybdenum, and vanadium have
produced interesting results in the synthesis of various sul-
foxides.[10–12] As a continuation to explore effective catalysts
used in sulfoxidation, in the present paper, a new benzo-
hydrazone compound, Nꢁ-(3-bromo-2-hydroxybenzylidene)-4-
nitrobenzohydrazide (H2L; Scheme 1), and its oxovanadium(V)
complex, 2[VOL(BHA)]·CH3CN, where HBHA is benzohy-
droxamic acid, were prepared and investigated for their peroxi-
dic oxidation on sulfides.
xybenzylidene)-4-nitrobenzohydrazide (H2L), and its oxovana-
dium(V) complex, 2[VOL(BHA)]·CH3CN, where HBHA is benzo-
hydroxamic acid, was prepared and structurally characterized by
physicochemical methods and single-crystal X-ray diffraction. The
benzohydrazone compound crystallizes in the monoclinic space
group P21/c, with a = 11.2211(15), b = 13.5515(18), c = 9.2850(10)
Å, β = 90.554(2)◦, V = 1411.8(30 Å3, Z = 4, R1 = 0.0757, and
wR2 = 0.1920. The oxovanadium(V) complex crystallizes in the
triclinic space group P–1, with a = 11.3754(13), b = 14.7186(19),
c = 15.611(2) Å, α = 83.952(2)◦, β = 72.346(2)◦, γ = 69.848(2)◦,
V = 2338.1(5) Å3, Z = 2, R1 = 0.0886, and wR2 = 0.2245. X-ray
structural analysis indicates that the benzohydrazone ligand co-
ordinates to the V atom through the phenolate O, imino N, and
enolic O atoms. The V atom in the complex is coordinated by one
benzohydrazone ligand and one BHA ligand, as well as one oxo O
atom, forming an octahedral coordination. The crystal structures
of the ligand and the complex are stabilized by hydrogen bonds.
The complex is an effective catalyst for sulfoxidation.
NO2
H
N
Supplemental materials are available for this article. Go to the
publisher’s online edition of Synthesis and Reactivity in Inorganic,
Metal-Organic, and Nano-Metal Chemistry to view the supplemen-
tal file.
N
O
OH
Br
Keywords benzohydrazone, crystal structure, oxovanadium com-
SCH. 1. H2L.
plex, sulfoxidation
EXPERIMENTAL
INTRODUCTION
All chemicals were of reagent grade and used as purchased.
Microanalyses of C, H, N were performed on a Perkin-Elmer-
2400 Series II CHN analyzer (Yunnan Normal University,
China). FT-IR spectra (4000–200 cm−1) of the ligand and the
complex were recorded on a Perkin-Elmer Spectrum RX I FT-
IR system (Yunnan Normal University, China) with solid KBr
pellets. 1H NMR spectra were recorded on Bruker Avance 200
spectrometer (Yunnan Normal University, China).
Schiff-base transition metal complexes have attracted much
attention in metallo-organic and coordination chemistry because
of their interesting structures and diverse range of applica-
tions,[1–4] especially for their catalytic properties.[5–7] Sulfoxides
Received 17 September 2012; accepted 10 November 2012.
The authors would like to acknowledge the support from Depart-
ment of Yunnan Province Education for the fund of Science Research
(Grant no. ZD2010003).
Address correspondence to Yong-Qing Su, Faculty of Chemistry &
Chemical Engineering, Yunnan Normal University, Kunming 650500,
P. R. China. E-mail: yongqing su@163.com
Synthesis of H2L
Equimolar quantities of 3-bromosalicylaldehyde (0.201 g,
1 mmol) and 4-nitrobenzohydrazide (0.181 g, 1 mmol) were
mixed in 50 mL methanol. The mixture was stirred at reflux for
677

678
Y.-Z. WANG ET AL.
30 min and the solvent was evaporated to give yellow crystalline The resulting deep brown solution was filtered and left undis-
product of H2L, which was used without further purification. turbed. After a few days, brown block shaped X-ray diffraction
Anal. Calcd. for C14H10BrN3O4: C, 46.2; H, 2,8; N, 11.5. Found: quality single crystals were formed and isolated by filtration.
C, 46.1; H, 2.7; N, 11.6%.
Yield: 33.7 mg (60%). Anal. Calcd. for C44H31Br2N9O14V2: C,
45.1; H, 2.7; N, 10.8. Found: C, 44.9; H, 2.7; N, 10.7%.
Synthesis of the Oxovanadium Complex
Crystallographic Data Collection and Structure
Refinements
H2L (36.4 mg, 0.1 mmol) and benzohydroxamic acid
(13.7 mg, 0.1 mmol) were dissolved in 15 mL methanol. The
solution was then added dropwise to a 10 mL gently warmed
Diffraction quality single crystals of H2L and the complex
methanol solution of VO(acac)2 (26.5 mg, 0.1 mmol). The mix- were mounted on a Bruker AXS SMART diffractometer (Yun-
ture was refluxed for 30 min and cooled to room temperature. nan Normal University, China) with a graphite monochromator
and Mo Kα radiation (λ = 0.71073 Å). The crystallographic
data collection was performed using multi-scan technique at
298(2) K. Data collection and the unit cell refinement were
performed using CrysAlisPRO software.[13] The structures of
the compounds were solved by direct method procedures with
SHELXS,[14] and refined by full-matrix least squares based on
F2 with SHELXL.[14] The non-hydrogen atoms were refined
with anisotropic factors. The amino H atoms in H2L and the
complex were located in difference Fourier maps and refined
isotropically, withN–Hdistances restrainedto0.90(1) Å. There-
maining hydrogen atoms were positioned geometrically treated
as riding on their parent atoms. The data collection and refine-
ment parameters are listed in Table 1. Selected bond lengths and
angles are given in Table 2.
TABLE 1
Crystal data and structure refinement for H2L and the complex
H2L
Complex
Empirical formula
Formula weight
Temperature (K)
Wavelength (Å)
Crystal system
Space group
Crystal color/shape
Unit cell dimensions
a (Å)
C14H10BrN3O4 C44H31Br2N9O14V2
364.2
298(2)
0.71073
1171.5
298(2)
0.71073
Triclinic
P–1
Monoclinic
P21/c
Yellow/block
Brown/block
11.2211(15)
13.5515(18)
9.2850(10)
90
90.554(2)
90
1411.8(3)
4
1.713
11.3754(13)
14.7186(19)
15.611(2)
83.952(2)
72.346(2)
69.848(2)
2338.1(5)
2
b (Å)
Catalytic Oxidation
c (Å)
The oxovanadium complex (0.001 M) and phenyl methyl
sulfide (0.1 M) were dissolved at room temperature in a
mixture of CH2Cl2 and CH3OH (6:4) together with 1,3,5-
trimethoxybenzene (0.1 M) as internal standard. The resulting
solution was cooled to 283 K and H2O2 (35% w/w) added drop-
wise (0.125 M). An aliquot of the reaction solution (2.0 mL)
was quenched with 5 mL of a stock solution of Na2SO3 (0.1 M)
at 60 min and 2 h, and extracted with dichlormethane (three
times 4 mL). From the collected organic phases the solvent was
removed under reduced pressure to complete dryness and the
residue redissolved in deuterated chloroform (0.6 mL) and ana-
lyzed by 1H NMR to determine the yields with reference to the
internal standard 1,3,5-trimethoxybenzene.
α (/◦)
β (/◦)
γ (/◦)
Volume (Å3)
Z
Density (calculated, g
1.664
cm−3
)
Absorption coefficient
(mm−1
F(000)
2.934
2.186
)
728
1.81–26.49
1172
2.72–25.00
θ range for data
collection (◦)
Reflections collected
Independent
10088
2817
14070
7425
RESULTS AND DISCUSSION
reflections
The condensation of 3-bromosalicylaldehyde with 4-
nitrobenzohydrazide in methanol with 1:1 stoichiometric ratio
gave yellow crystalline product of H2L. The benzohydrazone
ligand react with VO(acac)2 in the presence of benzohydrox-
amic acid yielded the oxovanadium complex. Elemental anal-
yses were found to be in good agreement with the formulae
calculated from the X-ray determination.
Observed reflections
[I > 2σ(I)]
Restraints
1818
4431
2
205
0.5778 and
0.6354
1.023
0
641
Parameters
Max. and min.
transmission
0.7642 and 0.8445
Goodness-of-fit on F2
Rint
1.016
0.0463
0.0886
0.0699
0.0757
IR Spectra
Final R indices [I >
2σ(I)]
R indices (all data)
The sharp absorption bands located at 3222 cm−1 in the
infrared spectrum of H2L and at 3289 cm−1 in the infrared
spectrum of the complex are attributed to the N–H stretches.
0.1920
0.2245

OXOVANADIUM(V) COMPLEX
679
TABLE 2
Selected bond lengths (Å) and bond angles (◦) for H2L and the
complex
H2L
Bond lengths
C7-N1
N2-C8
1.269(5)
1.343(6)
N1-N2
C8-O2
1.386(5)
1.228(5)
Bond angles
C7-N1-N2
N2-C8-O2
the complex
Bond lengths
V1-O1
V1-N1
V1-O6
V2-O8
V2-O13
116.9(4)
123.0(4)
N1-N2-C8
119.3(3)
FIG. 1. Molecular structure with atomic numbering for H2L. Hydrogen bond
is shown as a dashed line.
1.858(6)
2.074(7)
1.857(6)
1.879(6)
1.866(6)
2.079(7)
1.294(10)
1.305(11)
1.293(12)
1.296(11)
V1-O2
V1-O5
V1-O7
V2-O9
V2-O14
V2-O12
N1-N2
C8-O2
N5-N6
C29-O9
1.970(5)
2.202(6)
1.592(7)
1.935(6)
1.586(6)
2.243(6)
1.388(9)
group P21/c and the complex crystallizes in the triclinic space
group P–1.
In the free benzohydrazone molecule, there is an intramolec-
ular O1–H1···N1 hydrogen bond, which contributes to the pla-
narity of the benzene ring and the methylidene unit. The di-
hedral angle between the two benzene rings is 14.3(3)◦. The
oxovanadium complex, derived from H2L and benzohydrox-
V2-N5
C7-N1
N2-C8
C28-N5
1.307(10) amic acid, is a mononuclear compound. In the asymmetric unit
1.406(9)
of the complex, there are two independent complex molecules
1.303(10) and an acetonitrile molecule of crystallization. The benzohy-
N6-C29
Bond angles
O7-V1-O6
O6-V1-O1
O6-V1-O2
O7-V1-N1
O1-V1-N1
O7-V1-O5
O1-V1-O5
N1-V1-O5
O14-V2-O8
O14-V2-O9
O8-V2-O9
O13-V2-N5
O9-V2-N5
O13-V2-O12
O9-V2-O12
C7-N1-N2
N2-C8-O2
N5-N6-C29
drazone ligands form one five- and one six-membered chelate
95.0(3)
107.6(3)
89.1(2)
97.2(3)
84.3(3)
171.0(3)
82.0(2)
91.8(2)
99.0(3)
101.4(3)
152.1(3)
162.0(3)
75.0(3)
75.2(2)
80.1(2)
117.5(7)
121.8(8)
108.7(7)
O7-V1-O1
O7-V1-O2
O1-V1-O2
O6-V1-N1
O2-V1-N1
O6-V1-O5
O2-V1-O5
O14-V2-O13
O13-V2-O8
O13-V2-O9
O14-V2-N5
O8-V2-N5
O14-V2-O12
O8-V2-O12
N5-V2-O12
N1-N2-C8
C28-N5-N6
N6-C29-O9
99.5(3)
100.5(3)
152.7(3)
161.3(3)
74.8(2)
76.1(2)
81.2(2)
97.1(3)
104.8(3)
91.3(3)
97.1(3)
83.8(3)
172.2(3)
82.3(2)
90.7(2)
109.2(7)
116.6(7)
121.9(8)
rings with bite angles of 74.8(2)◦ and 84.3(3)◦ for one molecule
and 75.0(3)◦ and 83.8(3)◦ for the other. The benzohydroxamic
acid ligands form five-membered chelate rings with bite angles
of 76.1(2)◦ for one molecule and 75.2(2)◦ for the other. The
V1 and V2 atoms are in distorted octahedral O5N coordination
spheres. For the V1 coordination, the equatorial plane is defined
by the phenolate O1 atom, imine N1 atom, and enolic O2 atom
of the benzohydrazone ligand, and the O6 atom of the benzo-
hydroxamic acid ligand, and the axial positions are occupied by
the O5 atom of the benzohydroxamic acid ligand and one oxo
O7 atom. The displacement of the V1 atom from the equatorial
plane towards the axial oxo group is 0.263(1) Å. For the V2
The broad and weak bands indicative of the νO-H vibrations of
the hydroxyl groups of the ligand is centered at 3456 cm−1
.
The strong band observed at 1610 cm−1 is attributed to the
conjugated C=N–N=C moiety of the benzohydrazone ligand.
The middle band at 973 cm−1 is assigned to the V=O stretch.[15]
The bands due to ν(V–O) and ν(V–N) are occurred at 443, 530,
and 595 cm−1, respectively.
Structure Description of H2L and the Complex
Figures 1 and 2 give perspective views of H2L and the oxo-
FIG. 2. Molecular structure with atomic numbering for the complex. Hydrogen
vanadium(V) complex. H2L crystallizes in the monoclinic space bond is shown as a dashed line.

680
Y.-Z. WANG ET AL.
FIG. 3. Molecular packing diagram of H2L, viewed along the b-axis. Hydro-
gen bonds are shown as dashed lines.
coordination, the equatorial plane is defined by the phenolate
O8 atom, imine N5 atom, and enolic O9 atom of the benzohy-
drazone ligand, and the O13 atom of the benzohydroxamic acid
ligand, and the axial positions are occupied by the O12 atom of
the benzohydroxamic acid ligand and one oxo O14 atom. The
displacement of the V2 atom from the equatorial plane towards
the axial oxo group is 0.287(1) Å. The cis bond angles are in
the range 74.8(2)–107.6(3)◦, and the trans bond angles are in
the range 152.1(3)–171.0(3)◦, indicating the octahedral coordi-
nation is much distorted. The V–O and V–N bond lengths in
the complex are similar to those observed in other similar oxo-
vanadium(V) complexes with octahedral coordination.[16–18] In
the benzohydrazone ligands of the complex, the dihedral angles
between the two benzene rings are 8.6(3)◦ and 20.7(3)◦.
FIG. 4. Molecular packing diagram of the complex, viewed along the a-axis.
Hydrogen bonds are shown as dashed lines.
O
The coordination of H2L to the V atoms can be reflected
by the changes of the corresponding bond lengths and angles
(Table 2). The bond lengths of C7=N1, C28=N5, N1–N2, and
N5–N6 in the complex are much longer than the corresponding
bonds observed in H2L. However, the distances of C8–N2 and
C29–N6 in the complex are much shorter than C8–N2 in H2L,
and the distances of C8–O2 and C29–O9 in the complex are
much longer than C8–O2 in H2L, indicating the enolization of
the N2–C8–O2 and N6–C29–O9 groups in the complex.
S
S
the complex
H2O2 / TMB
SCH. 2. The oxidation reaction.
through intermolecular N–H···N hydrogen bonds (Table 3;
Figure 4).
Catalytic Property
In the crystal structure of H2L, benzohydrazone molecules
are linked through intermolecular N–H···O hydrogen bonds (Ta-
The catalytic oxidation test of the complex on the oxida-
ble 3), forming chains running along the c-axis (Figure 3). In the tion of sulfide under homogeneous conditions in solution using
crystal structure of the oxovanadium complex, the acetonitrile methyl phenyl sulfide as a substrate is shown as Scheme 2. As
molecules are linked to the oxovanadium complex molecules oxidant hydrogen peroxide was used in a slight excess of 1.25
TABLE 3
Distances (Å) and angles (◦) involving hydrogen bonding of H2L and the complex
D−H···A
d(D−H)
d(H···A)
d(D···A)
Angle(D−H···A)
H2L
O1−H1···N1
N2−H2···O2i
the complex
N8−H8A···N9
0.85(1)
0.90(1)
1.99(5)
2.07(2)
2.626(5)
2.911(4)
131(6)
156(5)
0.86
2.11
2.932(13)
159
Symmetry code for i: x, 3/2 – y, 1/2 + z.

OXOVANADIUM(V) COMPLEX
681
equivalents based on the sulfide substrate. Reactions were run
with 1 mol% of catalyst based on the substrate at a temperature
of 10◦C. NMR techniques have been used to monitor the forma-
tion of the sulfoxides with 1,3,5-trimethoxybenzene as internal
standard to determine the yields. The reaction was started by
the addition of hydrogen peroxide. A control reaction under the
same condition without any complex present leads to less than
1% sulfide conversion within 4 h. In the presence of the com-
plex conversion of 91% of sulfide to sulfoxide within 60 min
reaction time were observed. After about 2 h the conversion of
a total amount of sulfide was complete. Under the given condi-
tions no over oxidation to the sulfone could be detected. It can
be seen that the complex has effective catalytic property for the
sulfoxidation.
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CONCLUSION
In the present work, a new benzohydrazone compound Nꢁ-
(3-bromo-2-hydroxybenzylidene)-4-nitrobenzohydrazide, and
a new oxovanadium(V) complex derived from the benzohy-
drazone compound and benzohydroxamic acid have been suc-
cessively prepared and structurally characterized. The benzohy-
drazone ligand coordinates to the V atom through the phenolate
O, imino N, and enolic O atoms. The complex is an effective
catalyst for the sulfoxidation reaction of sulfide to sulfoxide.
SUPPLEMENTARY MATERIALS
Crystallographic data for the complexes have been deposited
with the Cambridge Crystallographic Data Centre (CCDC
901044 for H2L and 901045 for the complex). Copies of
these information may be obtained free of charge from the
Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK
(fax: +44–1223-336033; Email: deposit@ccdc.cam.ac.uk or
http://www.ccdc.cam.ac.uk).
12. Suresh, P.; Srimurugan, S.; Babu, B.; Pati, H.N. Asymmetric sulfoxidation
of prochiral sulfides using aminoalcohol derived chiral C-3-symmetric trin-
uclear vanadium Schiff base complexes. Tetrahedron 2007, 18, 2820–2827.
13. Bruker AXS. SAINT Software; Bruker AXS, Madison, WI, 1998.
14. Bruker AXS. SHELXTL Software; Bruker AXS, Madison, WI, 1998.
15. Monfared, H.H.; Alavi, S.; Bikas, R.; Vahedpour, M.; Mayer, P.
Vanadiumoxo-aroylhydrazone complexes: synthesis, structure and DFT
calculations. Polyhedron 2010, 29, 3355–3362.
16. Gao, S.; Weng, Z.-G.; Liu, S.-X. Syntheses and characterization of four
novel monooxovanadium(V) hydrazone complexes with hydroxamate or
alkoxide ligand. Polyhedron 1998, 17, 3595–3606.
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