Canadian journal of chemistry

Benzenesulfonyl chloride with primary and secondary amines in aqueous media Unexpected high conversions to sulfonamides at high pH

JF King, MS Gill, P Ciubotaru

Index: King, James F.; Gill, Manjinder S.; Ciubotaru, Petru Canadian Journal of Chemistry, 2005 , vol. 83, # 9 p. 1525 - 1535

Full Text: HTML

Citation Number: 12

Abstract

We have determined pH yield profiles under pseudo-first-order conditions of the reactions of benzenesulfonyl chloride with a set of primary and secondary water-soluble alkylamines, and have found with certain amines, such as dibutylamine, a profile taking the form of a sigmoid pH–yield curve with relatively high yields of the sulfonamide persisting with increasing basicity up to and including 1.0 mol/L sodium hydroxide. This behaviour is ...