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The second-order rate constants have been measured spectrophotometrically for the reactions of paraoxon 1 and parathion 2 with a series of alicyclic secondary amines, and ions in at . A linear Brnsted-type plot with = 0.40 was obtained for the reactions of 1 with amines and . The reaction has been concluded to proceed through a concerted mechanism. deviates positively from the linear Brnsted-type plot, implying that the -effect is operative. The magnitude of the -effect () was found to be ca. 55 for the reaction of 1 and 290 for that of parathion 2, indicating that is highly effective in decomposition of the toxic phosphorus compounds although it is over 4 units less basic than . Among the theories suggested as origins of the -effect (e.g., TS stabilization through an intramolecular Hbonding interaction, solvent effect, and polarizability effect), polarizability effect appears to be the most important factor for the -effect in this study, since the polarizable exhibits a larger -effect for the reaction of the more polarizable substrate 2.

Decomposition of Paraoxon and Parathion by Amines, HOO-and OH-Ions: Reaction Mechanism and Origin of the α-Effect

Decomposition of Paraoxon and Parathion by Amines, HOO^-and OH^-Ions: Reaction Mechanism and Origin of the α-Effect