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Mechanism of Hydrolysis of 2,2-Disubstituted Silocanes and Germocanes and 1-Substituted Silatranes and Germatranes

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Abstract

According to DFT quantum chemical calculations, hydrolysis of 2,2-disubstituted silocanes and germocanes is characterized by lower energies of activation and slightly lower positive Gibbs energies than the hydrolysis of the corresponding silatranes and germatranes. The annular configuration of the hydrolysis products is stabilized by the transannular interaction N→X (X = Si, Ge) and intramolecular hydrogen bonding.

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Authors and Affiliations

  1. Kazan (Volga Region) Federal University, ul. Kremlevskaya 18, Kazan, Tatarstan, 420008, Russia

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

  2. Kazan Branch, Joint Supercomputer Center of the Russian Academy of Sciences, ul. Lobachevskogo 2/31, Kazan, Tatarstan, 420111, Russia

    D. V. Chachkov

Authors
  1. Ya. A. Vereshchagina
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  2. D. V. Chachkov
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  3. R. R. Ismagilova
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  4. E. A. Vedeneeva
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Correspondence to Ya. A. Vereshchagina.

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Dedicated to Full Member of the Russian Academy of Sciences

I.P. Beletskaya on her jubilee

Original Russian Text © Ya.A. Vereshchagina, D.V. Chachkov, R.R. Ismagilova, E.A. Vedeneeva, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 3, pp. 482–492.

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Vereshchagina, Y.A., Chachkov, D.V., Ismagilova, R.R. et al. Mechanism of Hydrolysis of 2,2-Disubstituted Silocanes and Germocanes and 1-Substituted Silatranes and Germatranes. Russ J Org Chem 54, 490–499 (2018). https://doi.org/10.1134/S1070428018030181

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  • DOI: https://doi.org/10.1134/S1070428018030181

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