Effects of Amine Oxide Surfactants on Reactions of Bromide and Hydroxide Ions with Methylnaphthalene-2-Sulfonate.
The SN2 reaction of Br- with methylnaphthalene-2-sulfonate (MeONs) in water is accelerated by micelles of tetradecyldialkyl amine oxide (alkyl = methyl, n-propyl) and rates increase sharply in HBr due to increased binding of Br- to the protonated amine oxide. Second-order rate constants at the micellar surface are similar to those at surfaces of trialkylammonium and sulfobetaine micelles. The reaction of OH- with MeONs is weakly inhibited by amine oxide micelles, showing that dispersive, as well as coulombic and charge-dipole, forces play a major role in the association of ions with surfaces of micellar aggregates. Copyright 1999 Academic Press.
Brinchi
L
Dipartimento di Chimica, Università di Perugia, Perugia, 06100, Italy
Dionigi
C
Di Profio P
Germani
R
Savelli
G
Bunton
CA