The synthesis, characterization, and theoretical analysis of novel Si-substituted silylethyl derivatives of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole

Trifluorosilylethyl derivatives of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole C6H4NYCS(CH2)2SiF3 (Y = O, S) have been synthesized in order to study the intramolecular N → Si interaction in compounds with the SiCCSCN fragment. Ab initio and DFT calculations were performed to shed light on the electronic structure of these compounds. Silatranylethyl derivatives of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole C6H4NYCS(CH2)2Si(OCH2CH2)3N (Y = O, S) containing an intramolecular N → Si coordination bond and a pentacoordinate silicon atom were obtained as crystals. Their structures were confirmed by X-ray structural analysis. All compounds have been fully characterized by elemental analysis, IR and NMR spectroscopy and mass spectrometry.