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Reactivity of Benzamide toward Sulfonylation

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Abstract

The ranges of variation of the rate constant (0.031– 0.153 L·mol–1·s–1), energy of activation (21– 55 kJ/mol), and entropy of activation (88–191 J·mol–1·K–1) for the reaction of benzamide with 3-nitrobenzenesulfonyl chloride in aqueous 1,4-dioxane with a concentration of water of 15–40 wt % have been determined by studying the reaction kinetics in the temperature range 298–313 K. The potential energy surface for the gas-phase reaction of benzamide with 3-nitrobenzenesulfonyl chloride has been simulated at the DFT B3LYP/ 6-311G(d,p) level of theory; the results of quantum chemical simulation suggest bimolecular nucleophilic substitution mechanism of this reaction.

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Funding

This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation in the framework of state assignment to the Ivanovo State University for research activity (application no. FZZM-2021-0002).

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Authors and Affiliations

  1. Ivanovo State University, 1530250, Ivanovo, Russia

    T. P. Kustova, L. B. Kochetova & A. A. Kruglyakova

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  1. T. P. Kustova
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  2. L. B. Kochetova
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  3. A. A. Kruglyakova
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Correspondence to T. P. Kustova.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 7, pp. 1006–1011 https://doi.org/10.31857/S0514749221070107.

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Kustova, T.P., Kochetova, L.B. & Kruglyakova, A.A. Reactivity of Benzamide toward Sulfonylation. Russ J Org Chem 57, 1098–1102 (2021). https://doi.org/10.1134/S1070428021070101

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  • DOI: https://doi.org/10.1134/S1070428021070101

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