Are the interfacial basicities of aqueous cationic micelles and cationic reverse microemulsions different by orders of magnitude?

Abstract

Formation of 5-hexadecyl-7-methylindazole (16-Ind) from 2,6-dimethyl-4-hexadecylbenzenediazonium tetrafluoroborate (16-ArN₂⁺) bound to aqueous cationic micelles (prepared in aqueous buffers of p^H 7.0) has been shown to originate from the remarkably high interfacial basicity of aqueous cationic micelles. The rationale behind our conclusion is that formation of indazole from o-methylarenediazonium salts has never been observed if the medium of the diazonium salts is not basic. On the same ground, the absence of any 16-Ind product from 16-ArN₂⁺ in cationic reverse microemulsions is consistent with the interfacial basicities of cationic reverse microemulsions being significantly lower than that of cationic micelles.