N′-(3-Bromo-2-Hydroxybenzylidene)-4-nitrobenzohydrazide and Its Oxovanadium(V) Complex: Synthesis, Crystal Structures, and Catalytic Property

Abstract

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) Å, β = 90.554(2)°, V = 1411.8(30 ų, Z = 4, R ₁ = 0.0757, and wR ₂ = 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) ų, Z = 2, R ₁ = 0.0886, and wR ₂ = 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.

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Keywords:

• benzohydrazone
• crystal structure
• oxovanadium complex
• sulfoxidation

Acknowledgments

The authors would like to acknowledge the support from Department of Yunnan Province Education for the fund of Science Research (Grant no. ZD2010003).