Supernucleophilic Systems Underlain by Functionalized Surfactants in Cleavage of 4-Nitrophenyl Esters of Phosphorus and Sulfur Acids: IV. Micellar Effects of Functionalized Surfactants with a Variable Nature of the Head Group and Hydrophobicity in Transfer Reactions of the Phosphonyl Group

Abstract

[2-(Hydroxyimino)]dimethylalkylammonium bromides (Alk = C₁₆H₃₃, C₁₄H₂₉, C₁₂H₂₅) were synthesized and their reactivity was investigated in the cleavage of 4-nitrophenyl diethylphosphonate. The halfdegradation times of substrate vary in the series of C₁₆H₃₃ ≈ C₁₄H₂₉12H₂₅. In the case of surfactants containing imidazole and pyridine the micellar effects grow with growing hydrophobic properties of the alkyl substituent. In designing supernucleophilic systems for the cleavage of organophosphorus compounds the structural modification of surfactants should account for both the hydrophobic characteristics and the nature of the cationic group affecting the micellar structure.