Hydrolysis of Nicotinyl 6-Aminonicotinate

Abstract

The degradation kinetics of nicotinyl 6-aminonicotinate in aqueous buffer solutions were studied over the pH range from 4.0 to 10.0. In all cases, pseudo-first-order kinetics were observed at constant hydronium ion concentration. The pH-rate profile indicated that the hydrolysis of nicotinyl 6-aminonicotinate may be described by at least two catalytic terms. In alkaline solution the hydrolysis is catalyzed primarily by hydroxyl ions. In acidic solution the hydrolysis may be attributed to either the water-catalyzed reaction of the protonated species or the hydronium ion catalyzed reaction of the free base. The resulting catalytic profile afforded a sharp pH minimum of ˜5.90 at 65°C. An activation energy of 16 Kcal/mol was obtained in a phosphate buffer solution at a pH of ˜5.90 ∓ 0.2. The first- and second-order reaction constants for water and hydroxyl ion catalysis were determined, and the temperature dependency of the reaction was studied. The buffer effect and solvent effect on the hydronium and hydroxyl ion catalysis was also investigated.