Mechanistic studies of the Carbonate Esters hydrolysis catalized by imidazole.
DOI:
https://doi.org/10.5433/1679-0375.2000v21n4p59Keywords:
reaction mechanisms, chemical kinetics, carbonates.Abstract
Kinetic and mechanistic aspects of the imidazole-catalzed hydrolysis of p-nitrophenyl p-X-phenyl carbonates (X = MeO, Me, H, CI, CN, N02, series I) and bis (p-X-phenyl) carbonates (X = MeO, Me, H, Ci, N02, series II) were examined. Based on catalytic rate constants, activation parameters, kinetic solvent isotope effects, Hammett's r values, the following conclusions were reached: a) imidozole acts as nucleophilic catalyzer; b) the abandon group is a neutral phenol; c) the limiting rate step is the decomposition of the tetrahedral intermediate that precedes the p-X-phenoxycarbonylimidazole.
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