Mechanism of Hydrolysis of 1,1,1-Trisubstituted Hyposilatranes and Hypogermatranes

According to DFT calculations, hydrolysis of 1,1,1-trisubstituted hyposilatranes and hypogermatranes proceed in one stage and have lower activation energies than hydrolysis of the corresponding atranes and ocanes, and, unlike what is observed with the tricyclic and bicyclic analogs, the former react...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2019-02, Vol.55 (2), p.227-233
Main Authors: Vereshchagina, Ya. A., Ismagilova, R. R., Chachkov, D. V.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Germanium
Hydrogen bonding
Hydrolysis
Organic Chemistry
Silicon
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Summary:According to DFT calculations, hydrolysis of 1,1,1-trisubstituted hyposilatranes and hypogermatranes proceed in one stage and have lower activation energies than hydrolysis of the corresponding atranes and ocanes, and, unlike what is observed with the tricyclic and bicyclic analogs, the former reactions are characterized by positive Gibbs energies. The configuration of the hydrolysis products is stabilized by the transannular interactions N→X and O→X (X = Si, Ge) and intramolecular hydrogen bonding.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428019020143