Kinetic study on the hydrolysis of 1-N-naphtyl-phthalamic acid (Naptalam)

ALEJANDRO M. GRANADOS; MIRTHA NASSETTA; RITA H. DE ROSSI

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 1995 vol. 43 p. 2493 - 2496

0021-8561

The hydrolysis rate of l-N-naphthylphthalamic acid (Nap) was measured as a function of pH in the range of 0.9-5 and proceeds via undissociated neighboring carboxyl group participation as was proposed for other phthalamic acid derivatives. One of the main hydrolysis products is naphthy- lamine, which is a known carcinogenic agent. Nap is as reactive as phthalamic acid but is less reactive than phthalanilic acid. MMX calculations on phthalamic acid derivatives showed that phthalanilic acid has the closest distance for a most efficient intramolecular catalysis. Additives such as cyclodextrin or metal ion do not affect the kinetics of the reaction.