Neutral penta-coordinated diorganotin(IV) complexes derived from ortho-aminophenol Schiff bases: Synthesis, characterization and molecular structures

Abstract

The one pot reactions carried among ortho-aminophenol, R 2SnO (R = Me or Ph) and acetyl acetone, 2-hydroxyacetophenone and 2-hydroxy-3-methylacetophenone led to six new diorganotin(IV) compounds Me 2SnL1 ( 1), Ph 2SnL1 ( 2), Me 2SnL2 ( 3) Ph 2SnL2 ( 4), Me 2SnL3 ( 5) and Ph 2SnL3 ( 6) ( H2L1 = 2-(3-hydroxy-1-methyl-but-2-enylideneamino)-phenol, H2L2 and H2L3 = 2-[1-(2-hydroxyaryl)alkylideneamino]-phenol) in good yields. Combination of IR, 1H, 13C and 119Sn NMR and X-ray diffraction techniques along with elemental analyses evidenced the formation of penta-coordinated monomeric species. The crystal structures of ligand H2L1 and complexes 1, 3 and 4 were determined by single crystal X-ray diffraction study. In the solid state, the ligand H2L1 exists as keto-enamine tautomeric form. There are N–H…O intra-molecular hydrogen bonds between amine and carbonyl groups. Diorganotin(IV) complexes 1, 3 and 4 are monomers with TBP (trigonal bipyramidal) geometry surrounding the tin atom. The O, N, O- tridentate ligand places its two oxygen donating atoms in the axial positions, and the nitrogen atom occupies one equatorial position. The two R groups attached to tin occupy the other two equatorial positions. The solution structures were predicted by 119Sn NMR spectroscopy.