95115-18-7Relevant articles and documents
MECHANISM OF CATALYSIS BY 4-DIMETHYLAMINOPYRIDINE IN THE REACTION OF 4-DIMETHYLAMINOBENZOYL CHLORIDE WITH BENZYL ALCOHOLS IN METHYLENE CHLORIDE
Drizhd, L. P.,Bondarenko, L. I.,Litvinenko, L. M.,Savelova, V. A.,Kirichenko, A. I.
, p. 2181 - 2187 (2007/10/02)
The rate constants were measured for the forward and reverse reactions of the equilibrium process leading to the formation of the stable acylammonium salt from 4-dimethylaminobenzoyl chloride and 4-dimethylaminopyridine in methylene chloride at 25 deg C.The process is characterized by a high equilibrium constant (1.7*104 liter/mole).The kinetics of the reaction of the acylammonium salt N-(4-dimethylaminobenzoyl)-4-dimethylaminopyridinium chloride with benzyl alcohols RC6H4CH2OH (R = 4-CH3, H, 4-Br) under the same conditions were studied.It was shown that the process takes place by a stage mechanism; initially the adduct forms a complex with the alcohol reversibly, and the complex then dissociates into the final products in the slow rate-determining stage.This is a feature of nucleophilic catalysis by pyridine bases in the acylation of alcohols by carboxylic acid halides in a proton-inert medium.
