N′-(3-Bromo-2-hydroxybenzylidene)isonicotinohydrazide and its oxovanadium(V) complex: synthesis, structures, and catalytic properties

Abstract

A new hydrazone N′-(3-bromo-2-hydroxybenzylidene)isonicotinohydrazide (H 2 L) and its oxovanadium(V) complex, [VOLL′]·2H 2 O (L′ = 2-hydroxybenzohydroxamate), were prepared and structurally characterized by physico-chemical, spectroscopic methods, and single-crystal X-ray determination. The hydrazone coordinates to V through the phenolate oxygen, imino nitrogen, and enolate oxygen. The hydroxamate coordinates to V through the carbonyl oxygen and deprotonated hydroxyl oxygen. Vanadium in the complex is octahedral. The oxidation of olefins with the complex as catalyst was evaluated, which indicated that the complex showed catalytic efficiency in oxidation of several aliphatic and aromatic substrates under mild conditions, using tert-butyl hydrogen peroxide as oxidant.

Crystal structure of (E)-N′-(3-fluoro-2-hydroxybenzylidene)isonicotinohydrazide

“…A search of the Cambridge Structural Database (Version 5.38, latest update May 2017; Groom et al, 2016) for compounds with the (E)-N-(2-hydroxybenzylidene)isonicotinohydrazide skeleton revealed 86 hits. They include the isotypic crystal structures with bromide (PORYEC; Xiong & Li, 2014), methoxy (CANCOK, Yu et al, 2005;CANCOK01, Yang, 2007;CANCOK02, Xu, 2013), and hydroxy (WAFVEG; Tecer et al, 2010) groups substituted at the 3-position of the phenyl ring.…”