Kinetics of the N-chlorination of 2-aminobutyric, 3-aminobutyric, 3-aminoisobutyric and 4-aminobutyric acids in aqueous solution

We studied the kinetics of the N-chlorination of 2-aminobutyric, 3-aminoisobutyric, and 4-aminobutyric acids by sodium hypoclorite in strongly alkaline aqueous solution. As in the case of other amines, the rate of formation of the four N-chloroamino acids was proportional to the concentrations of hypochlorite and amino acid, and inversely proportional to the concentration of hydroxyl ions. A reaction mechanism compatible with these results is proposed and discussed. © John Wiley & Sons, Inc.