Concerted solvent processes for common sulfonyl chloride precursors used in the synthesis of sulfonamide-based drugs

被引：16

作者：

D'Souza, Malcolm J. ^{[1
]}

Yaakoubd, Lamia ^{[1
]}

Mlynarski, Stacey L. ^{[1
]}

Kevill, Dennis N. ^{[2
]}

机构：

[1] Wesley Coll, Dept Chem, Dover, DE 19901 USA

[2] No Illinois Univ, Dept Chem & Biochem, De Kalb, IL 60115 USA

来源：

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES | 2008年 / 9卷 / 05期

关键词：

solvolysis; sulfonyl transfer; 2-thiophenesulfonyl chloride; phenylmethanesulfonyl chloride; Grunwald-Winstein equation;

D O I：

10.3390/ijms9050914

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Specific rates of solvolysis in hydroxylic solvents available for the solvolysis of 2-thiophenesulfonyl chloride and phenylmethanesulfonyl chloride are supplemented by determining the values in fluoroalcohol-containing solvents. The data sets are then correlated using the extended Grunwald-Winstein equation. For both substrates, it is found that a single correlation controls the influence of solvent over the full range of solvent composition. The sensitivities to solvent nucleophilicity and solvent ionizing power are compared to values available for other substrates. Three of these previous studies are upgraded by the incorporation of additional specific rate values from the recent literature. With a methyl, isopropyl, benzyl, aromatic or heteroaromatic group as the R group of RSO2Cl, a concerted S(N)2 mechanism is proposed for the solvolysis.

引用

页码：914 / 925

页数：12

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