Journal of the American Chemical Society

Elimination-addition mechanisms of acyl group transfer: the hydrolysis and synthesis of carbamates

H Al-Rawi, A Williams

Index: Al-Rawi,H.; Williams,A. Journal of the American Chemical Society, 1977 , vol. 99, p. 2671 - 2678

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Citation Number: 32

Abstract

Abstract: The equilibrium constants for formation of aryl carbamates from isocyanic acid and a series of phenols have been measured. The Bronsted PN value for the reaction of phenolate anion with isocyanic acid and the selectivity of the equilibrium constant for formation of carbamate anion ArO-+ HNCO F! ArOC (NH) O-are consistent with a transition state half-way between reactants and product. The Bronsted selectivity for the latter ...