Mechanism of the hydrolysis reactions of 1-hydroxysilatrane and 1-hydroxygermatrane, 2,2-dihydroxysilocane and 2,2-dihydroxygermocane

GRAPHICAL ABSTRACT

ABSTRACT

The mechanism of the hydrolysis reactions of 2,2-dihydroxysilocane, 2,2-dihydroxygermocane, 1-hydroxysilatrane, and 1-hydroxygermatrane was studied by the density functional theory method. According to the quantum chemical calculations, the reactions of hydrolysis for 2,2-dihydroxysilocane and 2,2-dihydroxygermocane are characterized by the lower values of activation energy than for 1-hydroxysilatrane and 1-hydroxygermatrane. The ring configurations of the hydrolysis products are stable due to the presence of transannular interaction N→X (X = Si, Ge) and intramolecular hydrogen bond in their molecules.

KEYWORDS:

• Silocanes
• germocanes
• atranes
• reaction mechanism
• quantum chemical calculations

Funding

This work was supported by the Russian Foundation for Basic Research (Grant 13-03-00067-a).