Kinetic and theoretical study on nucleofugality in the phenolysis of 3-nitrophenyl and 4-nitrophenyl 4-cyanophenyl thionocarbonates

…, M Cepeda, P Pavez, R Contreras, JG Santos

Index: Castro, Enrique A.; Canete, Alvaro; Campodonico, Paola R.; Cepeda, Marjorie; Pavez, Paulina; Contreras, Renato; Santos, Jose G. Chemical Physics Letters, 2013 , vol. 572, p. 130 - 135

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Citation Number: 2

Abstract

The phenolysis of 3-nitrophenyl 4-cyanophenyl thionocarbonate (1) and 4-nitrophenyl 4- cyanophenyl thionocarbonate (2) are subjected to a kinetic investigation in order to evaluate the nucleofugality of the corresponding leaving groups. For the reaction of 2 only 4- nitrophenoxide is obtained as leaving group. For the reaction of 1 the nucleofugality ratio 3- nitrophenoxide/4-cyanophenoxide is 1/3 from the corresponding T− intermediate. ...