Supernucleophilic systems based on functionalized surfactants in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids: I. Reactivity of a hydroxyimino derivative of gemini imidazolium surfactant

A new functionalized gemini surfactant, 3,3′-2-(hydroxyimino)propane-1,3-diyl]bis(1-dodecyl-1H-imidazol-3-ium) dichloride, and its non-micelle-forming methyl analog, were synthesized. Nucleophilicity of the oximate group in these compounds in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids follows Brønsted relations for monomeric functionalized surfactants and non-micelle-forming oximes. As compared to the single-chained analog, the gemini surfactant ensured the same observed rate of substrate decomposition at lower concentration and lower pH. Micellar effects of the gemini surfactant in these reactions attain a value of ～10³ and are determined mainly by substrate concentration in the micellar pseudophase.