Abstract
Abstract Rate constants of reactions of OH- with thiol and thione phosphorus (V) esters are increased by cationic surfactants, cetyltrimethylammonium bromide, and mesylate (CTAX, X = Br, OMs) and there are double rate maxima at [CTAX] ≈ the critical micelle concentration (cmc). The esters are R′2 PO · SR, 1a, R′ = OEt; R = Ph; 1bR ′ = R = Ph; 1c, R′ = Ph, R = OEt and Parathion, (EtO)2 PS · OC6H4NO2 (4). In CTAOMs maximum rate enhancements are by factors of ca. 20 in 0.01 M OH- and are slightly lower in CTABr and at higher [OH-]. Changes in 1 H chemical shifts of CTAOMs on addition of 1b show that complexes form below the cmc. Reaction of OH- with 1b is speeded by tri-n-octyl methylammonium mesylate. These results show that submicellar complexes of substrate and hydrophobic ammonium ions are more reactive towards OH- than free substrate.
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