Concerted acetyl-group transfer between substituted phenolate ion nucleophiles: variation of transition-state structure as a function of substituent

S Ba-Saif, AK Luthra, A Williams

Index: Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew Journal of the American Chemical Society, 1989 , vol. 111, # 7 p. 2647 - 2652

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Citation Number: 130

Abstract

Abstract: Second-order rate constants (k,) have been measured for the concerted displacement of aryl oxide from aryl acetates in aqueous solution by substituted phenoxide ions. Values of kArO obey linear Brmsted correlations when either the leaving group or the attacking phenolate ion structures are varied. The Brmsted coefficients obey the equations p,,,= 0.20 pK,,-0.68 and PI,= 0.15 pKn,-1.73 to a good degree of precision, and the ...

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