Role of the hydrophobic properties of functional detergents on micellar effects in the dissociation of environmental toxicants

1-Alkyl-3-(2-oximinopropyl)imidazolium chlorides were prepared with different alkyl chain lengths (Alk = C₁₂H₂₅, C₁₄H₂₉). Some physicochemical indices (CMC and pK _a^app) were determined. The reactivity of these compounds was studied in the dissociation of 4-nitrophenyl esters of diethylphosphonic, diethylphosphoric, and toluenesulfonic acids. The times for 50% conversion of the substrates into reaction products decrease in the series: C₁₂H₂₅ > C₁₄H₂₉ >C₁₆H₃₃. In selecting the direction of modification of the supernucleophilic functional surfactants, we should take into account not only their hydrophobic properties but also the efficiency of substrate solubilization as well as the reactivity of the oximate group in the surfactant micelles.