Bulletin of the Korean Chemical Society

Aminolysis of S-4-Nitrophenyl X-Substituted Thiobenzoates: Effect of Nonleaving-Group Substituents on Reactivity and Mechanism

LR Im, SE Jeon, IH Um

Index: Im, Li-Ra; Jeon, Sang-Eun; Um, Ik-Hwan Bulletin of the Korean Chemical Society, 2011 , vol. 32, # 4 p. 1153 - 1157

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Abstract

Abstract A kinetic study is reported for aminolysis of S-4-nitrophenyl X-substituted thiobenzoates 3a-g in 80 mol%/20 mol% DMSO at. Thiol esters 3a-g are 7.8-47.6 fold more reactive than the corresponding oxygen esters (ie, 4-nitrophenyl X-substituted benzoates 1a- g). Such reactivity order appears to be in accordance with the expectation that 4- nitrothiophenoxide in 3a-g is a better nucleofuge than 4-nitrophenoxide in 1a-g since the ...