The synthesis and structural characterization of some triorganotin(IV) complexes of 2-{[(E)-1-(2-hydroxyaryl)alkylidene]amino}acetic acid. Crystal and molecular structures of Ph3Sn(2-OHC6H4C(H)NCH2COO) and Me3Sn(2-OHC6H4C(CH3)NCH2COO)

Triorganotin(IV) derivatives of 2-{[(E)-1-(2-hydroxyaryl)alkylidene]amino}acetic acid have been synthesized and characterized by 1H, 13C, 119Sn-NMR, 119Sn Mössbauer and IR spectroscopic techniques in combination with elemental analyses. The crystal structures of triphenyltin 2-{[(E)-1-(2-hydroxyphenyl)methylidene]amino}acetate and trimethyltin 2-{[(E)-1-(2-hydroxyphenyl)ethylidene]amino}acetate are reported. The X-ray structures reveal that the complexes adopt a polymeric trans-O2SnC3 trigonal bipyramidal configuration with the R groups in the equatorial positions and the axial locations occupied by a carboxylate oxygen from the ligand and the phenolic oxygen of the ligand on an adjacent complex. The ligands coordinate in the zwitterionic form with the phenolic proton moved to the nearby nitrogen atom. There is hydrogen bonding between this proton and the phenolic oxygen. The carboxylate group is unidentate. The spectroscopic evidence in combination with 119Sn Mössbauer data suggest that the other complexes adopt similar polymeric structures in the solid state.