General Base Catalysis of Hydrolysis of Alkylaminoethyl Esters of Carboxylic Acids

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General base-catalyzed hydrolysis for several choline salt esters of carboxylic acids as well as succinylcholine chloride was investigated. Acetylcholine chloride, a part of succinylcholine chloride molecule, also was subject to general base-catalyzed hydrolysis. The ratio, kAC- to kOH-, of acetylcholine chloride was almost equal in magnitude to that of succinylcholine chloride. Degree of the influence of catalytic effect of general bases on the overall rate constant of ester hydrolysis was discussed. Imidazole was a less effective catalyst than phosphate dianion for the hydrolysis of the choline salt esters of carboxylic acids. The general base-catalyzed hydrolysis for these esters appears to represent classical general base catalysis rather than nucleophilic catalysis, as shown in the catalytic hydrolysis for the esters activated in acyl portion, enthyl haloacetates.5) An attempt was made to compare the effect of acetate ions on the hydrolytic rate constants of the Choline salt esters with that of the corresponding tertiary aminoesters. The catalytic contribution of acetate ions for the latter esters became less pronounced. The logarithms of rate constants of alkaline hydrolysis and acetate ion catalysis were not linearly related.

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