Concertedness in acyl group transfer in solution: a single transition state in acetyl group transfer between phenolate ion nucleophiles

S Ba-Saif, AK Luthra, A Williams

Index: Ba-Saif, Salem; Luthra, Ajay K.; Williams, Andrew Journal of the American Chemical Society, 1987 , vol. 109, # 21 p. 6362 - 6368

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Citation Number: 145

Abstract

Abstract: Rate constants have been measured for nucleophilic substitution of 4-nitrophenol from 4-nitrophenyl acetate by a series of phenolate anions. The Brernsted type plot is linear for unhindered phenolate ions with pK, values significantly above and below that of the displaced 4-nitrophenol:(log kArO= 0.75 pKAroH-7.28; n= 17, r= 0.984); this is consistent with a mechanism involving a single transition state or a mechanism with an intermediate ...