Mechanism of the periodate oxidation of ethane-1,2-diamine, NN′-dimethylethane-1,2-diamine, and 2-aminoethanol

Abstract

The kinetics of the oxidation by periodate of ethane-1,2-diamine, NN′-dimethylethane-1,2-diamine, and 2-aminoethanol have been studied at pH 4–12 and 293.2 K. The reaction rates are highest at pH 9–11. It is assumed that periodate monoanion reacts with the unprotonated amines. The reactions of 1,2-diamines with periodate are catalysed by acids and bases. The oxidation of 2-aminoethanol is catalysed by bases, and at high concentration of catalysts the rate seems to approach a limiting value. The pH dependence of the rate of oxidation of these compounds can be explained in terms of multi-stage reactions similar to those in the oxidation of 1,2-diols by periodate.