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The Role of Hydrogen Bond in the Mechanism of Autocatalytic Reaction between Acetic Anhydride and tert-Butyl Hydroperoxide

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Abstract

The role of hydrogen bonding in the autocatalytic reaction of acetic anhydride with tert-butyl hydroperoxide in CC14 has been elucidated. The stage-by-stage mechanisms of formation of hydrogen-bonded complexes. Structure and energy parameters of stable conformers of the compounds and energy of the major and transition states have been determined by means of B3LYP/aug-cc-pVDZ and B3LYP/aug-cc-pVTZ methods. The contribution of the O···HO hydrogen bonds in the stabilization of the complexes has been determined using the noncovalent interactions index. 1-Hydroxy-1-alkylperoxy compound is the most stable intermediate.

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  1. Korolev Samara National Research University, Moskovskoe sh. 34, Samara, 443086, Russia

    V. V. Varfolomeeva

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  1. V. V. Varfolomeeva
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Correspondence to V. V. Varfolomeeva.

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Original Russian Text © V.V. Varfolomeeva, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 5, pp. 710–716.

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Varfolomeeva, V.V. The Role of Hydrogen Bond in the Mechanism of Autocatalytic Reaction between Acetic Anhydride and tert-Butyl Hydroperoxide. Russ J Gen Chem 88, 855–861 (2018). https://doi.org/10.1134/S107036321805002X

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  • DOI: https://doi.org/10.1134/S107036321805002X

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