54437-71-7Relevant articles and documents
N-alkylation of N-monosubstituted sulfonamides in ionic liquids
Hu, Yi,Chen, Zhen-Chu,Le, Zhang-Gao,Zheng, Qin-Guo
, p. 347 - 351 (2007/10/03)
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Acid-catalyzed hydrolysis of benzenesulfonamides. Rate enhancements by ortho-alkyl substituents
Wagenaar, Anno,Kirby, Anthony J.,Engberts, Jan B. F. N.
, p. 203 - 205 (2007/10/02)
Pseudo-first-order rate constants have been measured for the acid-catalyzed hydrolysis of a series of N,N-dimethyl- and N-methyl-N-phenylbenzenesulfonamides in 70 percent (v/v) CF3CO2H/H2O at 99 deg C.Analysis of the effect of the alkyl substituents in the benzene ring shows a remarkable rate enhancement by ortho-alkyl groups, in the contrast with a rate retardation of similar substituents in the corresponding benzamides.The rate enhancement in the sulfonamides is attributed to relief of initalstate strain in the transition state for hydrolysis.When the sulfonamide moiety is contained in a five-membered ring fused to a phenyl ring, the rate of hydrolysis is markedly reduced by an ortho-methyl substituent.