Hydrolysis of N-methylnicotinyl and N-methylisonicotinyl esters and some n-participating derivatives under micellar conditions

Abstract

Hydrolysis rate of two types of compounds, A and B were studied in the presence of variable concentrations of an anionic surfactant (sodium dodecylsulfate, SDS). Class A of compounds consists of substances which hydrolyze by the S N1 mechanism and which are structurally related to cationic surfactants. The second class (B) contains an internal nucleophile and thus solvolyzes under anchimeric assistance. It was found that compounds of class A are forming an effective micelle and show a rate retardation relative to solvolysis in pure water. The hydrolysis rates of compounds of class B are relatively unaffected by the presence of the micelle forming surfactant. The merits of a N-methylnicotinoic and N-nethylisonicotinoic esters as a new type of leaving groups are discussed.