Collect. Czech. Chem. Commun. 1988, 53, 571-580

13C and 119Sn NMR evidence of the presence and extent of σ-π conjugation in some benzyltin compounds and their complexes

Jaroslav Holečeka, Antonín Lyčkab, Karel Handlířa and Milan Nádvorníka

a Department of General and Inorganic Chemistry Institute of Chemical Technology, 532 10 Pardubice
b Research Institute of Organic Syntheses, 532 18 Pardubice-Rybitví


The 13C and 119Sn NMR spectroscopy has been used to study the compounds types (C6H5CH2)4-nSn(CH3)n and (C6H5CH2)4-nSnCln (n = 0 - 3) in media of non-coordinating (deuteriochloroform) and coordinating (hexadeuteriomethyl sulphoxide) solvents. The analysis of the NMR data has confirmed the presence and established the relative extent of participation of the σ-π conjugative connection of the polarized σ(Sn-C) bond with the adjacent π electronic system of the aromatic ring in the Sn-CH2-C6H5 grouping. The extent of σ-π conjugation decreases with decreasing number of methyl groups in the compounds (C6H5CH2)4-nSn(CH3)n and with increasing number of chlorine atoms in the compounds (C6H5CH2)4-nSnCln and with increasing coordination number of the central tin atom in the complexes of the compounds (C6H5CH2)4-nSnCln.x(C2H3)2SO.