Leaving group tendencies and the rates of mono-oxygen donation by hydrogen peroxide, organic hydroperoxides, and peroxycarboxylic acids

Abstract

The log of the second-order rate constants for the sulphoxidation of thioxan, N-oxidation of N,N-dimethylbenzylamine, and oxidation of I^– to I₂ are linearly related to the pK_a of YOH when the mono-oxygen donors YOOH represent peroxycarboxylic acid, organic hydroperoxides, and hydrogen peroxide (the mechanism of mono-oxygenations by the biologically important 4a-hydroperoxyflavins find explanation through this correlation).