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

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Abstract

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.

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Authors and Affiliations

  1. Kazan Federal University, ul. Kremlevskaya 18, Kazan, Tatarstan, 420008, Russia

    Ya. A. Vereshchagina, R. R. Ismagilova & D. V. Chachkov

  2. Kazan Department of Joint Supercomputer Center of Russian Academy of Sciences — Branch of Federal State Institution “Scientific Research Institute for System Analysis of the RAS”, ul. Lobachevskogo 2/31, Kazan, Tatarstan, 420111, Russia

    D. V. Chachkov

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  1. Ya. A. Vereshchagina
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  2. R. R. Ismagilova
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  3. D. V. Chachkov
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Correspondence to Ya. A. Vereshchagina.

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Russian Text © Ya.A. Vereshchagina, R.R. Ismagilova, D.V. Chachkov, 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 2, pp. 279–286.

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Vereshchagina, Y.A., Ismagilova, R.R. & Chachkov, D.V. Mechanism of Hydrolysis of 1,1,1-Trisubstituted Hyposilatranes and Hypogermatranes. Russ J Org Chem 55, 227–233 (2019). https://doi.org/10.1134/S1070428019020143

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  • DOI: https://doi.org/10.1134/S1070428019020143

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