Synthesis and reactivity of novel 3-isothiocyanatopropylsilatrane derived from aminopropylsilatrane: X-ray crystal structure and theoretical studies

A novel silatrane containing Si ← N bond (2.160 Å), has been synthesized by the reaction of 3-aminopropylsilatrane (1), dicyclohexylcarbodiimide (2) and CS2. The structure was established by elemental analysis, spectroscopic methods (IR, 1H NMR, 13C NMR and Mass spectroscopy) and X-ray crystallography. It was correlated with theoretical studies such as semiempirical (AM1, PM3, PM3MM and MNDO), Density Functional Theory (B3LYP) and Hartree–Fock at 3-21+G∗ and 6-31G∗(d) levels. The reactivity of compound 3 was studied with some Lewis acids and bases that showed the formation of corresponding adducts (4–7), which were characterized by elemental analysis, IR and NMR (1H, 13C) spectroscopy.

Graphical abstractA novel silatrane 3-isothiocyanatopropylsilatrane has been synthesized and characterized by elemental analysis, spectroscopic methods and X-ray crystallography. The structure was correlated with theoretical studies such as semiempirical (AM1, PM3, PM3MM and MNDO), Density Functional Theory (B3LYP) and Hartree–Fock at 3-21+G∗ and 6-31G∗(d) levels. The reactivity of compound was also studied with some Lewis acids and bases.Figure optionsDownload full-size imageDownload as PowerPoint slide