REACTION MECHANISM OF THE BUFFER-CATALYZED AND SUBSTITUTED BETA-CYCLODEXTRIN - CATALYZED HYDROLYSIS OF CATECHOL CYCLIC PHOSPHATES.

摘要

The mechanism for the imidazole-catalyzed hydrolysis of catechol cyclic phosphate has been investigated. The Bronsted ;Based on the ;The proton inventory plots for the imidazole-catalyzed hydrolysis of catechol cyclic phosphate at buffer ratios 75:25, 50:50, and 25:75 (imidazole): (imidazolium) were dome-shaped, linear, and bowl-shaped, respectively. These different proton inventories indicate that the rate determining step of the reaction changes with the (imidazole): (imidazolium) ratio and, thus, supports a stepwise mechanism for this reaction. An inverse solvent isotope effect for the hydroxide catalyzed hydrolysis of catechol cyclic phosphate (k(D