Journal of the Chemical Society. Perkin transactions II p. 1233 - 1238 (1984)
Update date:2022-08-04
Topics:
Sabbagh, Mohamed Mowafak Al
Calmon, Michelle
Calmon, Jean-Pierre
The kinetics of hydrolysis of aryl and alkyl 4-phenylallophanates to phenyl urea and phenol or alcohol are studied.Acid-base catalysis, deuterium solvent isotope effects, and entropy of activation provide good evidence for a changeover in mechanism from E1cB for aryl allophanates to BAc2 for alkyl esters.The parameters of Hammett and Yukawa-Tsuno relationships for aryl esters and the non-linear Bronsted correlation with the pKa values of the leaving groups are in good agreement with the proposed mechanism.
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