Failure of the Pseudophase Model in the Acid-Catalyzed Hydrolysis of Acetals and p-Methoxybenzaldoxime Esters in the Presence of an Anionic Micelle

Article abstract of DOI:10.1021/j100253a016

The pseudophase model for micelle-catalyzed bimolecular reactions was tested for the acid-catalyzed hydrolysis of 2-(p-nitrophenyl)-1,3-dioxolane (1), acetyl p-methoxybenzaldoxime (2), and octanoyl p-methoxybenzaldoxime (3) in the presence of sodium dodecyl sulfate (SDS).At high acid concentrations the experimental data deviate appreciably from the behavior expected from the classical model.These discrepancies point to an additional catalytic pathway across the interfacial boundary operating at high +>.This additional pathway in micelle-catalyzed reactions seems to be of general occurence, and its existence cannot be overlooked in a complete theoretical description of catalytic micellar processes.