Mononuclear and dinuclear chiral vanadium(V) complexes with tridentate Schiff bases derived from R(−)-1,2-diaminopropane: Synthesis, structure, characterization and catalytic properties

A series of vanadium(V) complexes with unsymmetrical tridentate Schiff base ligands, obtained by the single condensation of R(−)-1,2-diaminopropane with salicylaldehyde and its derivatives, 2-hydroxy-1-naphthaldehyde, 2-hydroxyacetophenone, 1-hydroxy-2-acetonaphthone and 2-hydroxybenzophenone, were prepared. The complexes were characterized by elemental analysis and by their IR, CD, UV–Vis, 1D (1H, 51V) and 2D (COSY, NOESY, gHSQC) NMR spectra. Crystal structures of the mononuclear complex {R(−)-2-amino-1-N-[(2′-oxido-κO-4′,6′-dimethoxyphenyl)methylene]aminopropane-κ2N}dioxidovanadium(V), VO2(C12H17N2O3), 4, and of the dinuclear complex, di-μ-oxido-bis({R(−)-2-[1-(2-aminopropylimino)ethyl]-4-methylphenolato-κ3N,N′,O}oxidovanadium(V)), V2O4(C11H15N2O)2, 5, have been obtained by X-ray diffraction studies. The structure of 4 was revealed to be a distorted trigonal–bipyramidal coordination geometry, rarely encountered in VO2(tridentate Schiff base) complexes. Complexes 2 and 3 have the ability to catalyze the oxidation of prochiral sulfide substrates PhSR (R = Me, Bz) utilizing hydrogen peroxide or cumene hydroperoxide (CHPO) as the oxidant.

Graphical abstractA series of vanadium(V) complexes with unsymmetrical tridentate Schiff base ligands, obtained by the single condensation of R(−)-1,2-diaminopropane with carbonyl compounds, were prepared. The crystal structures of a mononuclear and a dinuclear complex have been obtained. The structure of the mononuclear compound revealed a distorted trigonal–bipyramidal coordination geometry, rarely encountered in VO2(tridentate Schiff base) complexes. Two of the complexes have the ability to catalyze the oxidation of prochiral sulfide substrates.Figure optionsDownload full-size imageDownload as PowerPoint slide