Chlorodiphenyltin(IV) and triphenyltin(IV) complexes of N-alkylated 2-amino-1-cyclopentene-1-carbodithioic acids: synthesis, spectroscopic characterization and X-ray studies

Four new complexes, [Ph3Sn(isopropylACDA)] (1), [Ph2SnCl(isopropylACDA)] (2), [Ph3Sn(secbutylACDA)] (3), and [Ph2SnCl(secbutylACDA)] (4), have been prepared from reaction between N-alkylated 2-amino-1-cyclopentene-1-carbodithioic acids (ACDA) with Ph2SnCl2 and Ph3SnCl in 1:1 ratio. All complexes are characterized by FTIR, multinuclear NMR (H-1, C-13, and Sn-119) and mass spectrometry. In all complexes, the S-H proton has been removed and coordination takes place through the carbodithioate moiety. The Sn-119 NMR data are consistent with five coordination of tin atom in solution. Complexes 2, 3, and 4 have also been confirmed by single X-ray crystallography. All three crystals are triclinic with space group P - 1. In complexes 2 and 4, the geometry around tin atom is distorted trigonal bipyramidal while in 3 the geometry is in between distorted tetrahedral and trigonal bipyramid. In all three structures, ligands are asymmetrically coordinated to tin atom. In addition, crystal structures are further stabilized by N-H center dot center dot center dot S hydrogen bonding.