Arenesulfonylation of N-alkylanilines: reaction kinetics and mechanism

被引：1

作者：

Kochetova, L. B. ^{[1
]}

Kustova, T. P. ^{[1
]}

Kuritsyn, L. V. ^{[1
]}

Katushkin, A. A. ^{[1
]}

机构：

[1] Ivanovo State Univ, 39 Ul Ermaka, Ivanovo 153025, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2017年 / 66卷 / 06期

关键词：

sulfonylation; N-alkylanilines; arenesulfonyl chlorides; aqueous organic solvents; quantum chemical simulation; reactions mechanisms; INFRARED DEPLETION SPECTROSCOPY; MOLECULAR-STRUCTURE; ANILINE-WATER; COMPLEX; SULFONAMIDES; CHLORIDES; SPECTRUM; ACIDS;

D O I：

10.1007/s11172-017-1846-0

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Kinetic regularities of arenesulfonylation of N-alkylanilines in binary water-organic solvents of variable composition have been studied. The rate constants for these reactions increase with increasing the water content in a system. The steric factor has the decisive influence on reactivity of N-alkylamines. The character of the influence of the composition and nature of a solvent on the rate constants for arenesulfonylation was discussed with the assistance of results of quantum chemical simulation of molecular complexes of the nucleophiles studied with the components of the binary systems. Calculation of potential energy surface for the reaction of N-methylaniline with benzenesulfonyl chloride showed that in the gas phase the process occurs by the S(N)2 mechanism.

引用

页码：999 / 1006

页数：8

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