Reactivity of 2-Sulfobenzoic Acid Imide and Benzenesulfonamide in Arenesulfonylation


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Abstract

Experimental study of the kinetics of the reactions of 2-sulfobenzoic acid imide (saccharin) and benzenesulfonamide with 3-nitrobenzenesulfonyl chloride in a 1,4-dioxane-water mixture (80:20 by weight) in the temperature range 298–318 K has shown that both compounds are low reactive (k298 = 1.66 × 10−4 and 3.37 × 10−3 L mol−1 s−1, respectively). The activation barriers to these reactions exceed 50 kJ/mol. Aqueous dioxane can be recommended as a solvent for the preparation of N-(benzenesulfonyl)-3-nitrobenzenesulfonamide in up to 87% yield.

About the authors

T. P. Kustova

Ivanovo State University

Author for correspondence.
Email: kustova_t@mail.ru
Russian Federation, Ivanovo

M. A. Agafonov

Ivanovo State University

Email: kustova_t@mail.ru
Russian Federation, Ivanovo

A. A. Kruglyakova

Ivanovo State University

Email: kustova_t@mail.ru
Russian Federation, Ivanovo

L. B. Kochetova

Ivanovo State University

Email: kustova_t@mail.ru
Russian Federation, Ivanovo

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