EXCITED-STATE, PROTON-TRANSFER REACTIONS OF SUBSTITUTED NAPHTHOLS IN MICELLES - COMPARATIVE-STUDY OF REACTIONS OF 2-NAPHTHOL AND ITS LONG-CHAIN ALKYL DERIVATIVES IN MICELLAR SOLUTIONS OF CETYLTRIMETHYLAMMONIUMBROMIDE

Excited-state, proton-transfer (ESPT) reactions of 2-naphthol and its long-chain alkyl derivatives (6-hexadecyl-2-naphthol and 1-octadecyl-2 -naphthol) were investigated in micellar solutions of cetyltrimethylam monium bromide (CTAB) and in ethanol solutions. Significant slowing do wn (by a factor of five to eight) of the photodissociation of 2-naphth ol containing alkyl groups in comparison with non-substituted 2-naphth ol was observed in CTAB micelles, in contrast with ethanol solutions w here the rate constants of ESPT reactions with the acetate anion for a -naphthol and its long-chain alkyl derivatives are similar. Experiment al results are rationalized in terms of the effect of the specific loc alization of the naphthol and naphtholate moieties of different hydrop hobicity in the micelles and of the relationship between the kinetic a nd thermodynamic parameters of ESPT.