Micellar effects on the hydrolysis of benzylidene-t-butylamine n-oxide and 3-phenyl-2-t-butyloxaziridine

Abstract

Micellar sodium dodecyl sulphate (NaLS) enhances the rate constants for the hydrolysis of benzylidene-t-butyl-amine N-oxide and -phenyl-2-t-butyloxaziridine by factors of 40 and 68, respectively. Hexadecyltrimethyl-ammonium bromide and 3-(dodecylmethylammonio)propane-1-sulphonate have no effects on the rates while polyoxyethylene(15)nonylphenol (lgepal CO-730) and 3-(dodecyldimethylammonio)propane-1-sulphonate enhance them slightly. Catalysis by NaLS of these two compounds is quite similar and originates from binding to the negatively charged micelle where the common intermediate, the positively charged protonated nitrone, and the transition state for the rate-limiting steps are stabilized.