Effect of cationic micelles on the E1cb mechanism of the hydrolysis of substituted p-nitrophenyl acetate
Abstract
The hydrolysis of XCH2CO2C6H4NO2-p catalysed by cetyltrimethylammonium bromide experiences a much larger micellar effect with XO2NC6H4 and PhS than with MeOC6H4 and PhO, in accord with the change in acidity of CH2group and suggesting a change of mechanism from ordinary addition-elimination under non-micellar conditions to an E1cB mechanism under micellar conditions.