A. Granados et al., KINETIC-STUDY ON THE HYDROLYSIS OF 1-N-NAPHTHYLPHTHALAMIC ACID (NAPTALAM), Journal of agricultural and food chemistry, 43(9), 1995, pp. 2493-2496
The hydrolysis rate of 1-N-naphthylphthalamic acid (Nap) was measured
as a function of pH in the range of 0.9-5 and proceeds via undissociat
ed neighboring carboxyl group participation as was proposed for other
phthalamic acid derivatives. One of the main hydrolysis products is na
phthy-lamine, which is a known carcinogenic agent. Nap is as reactive
as phthalamic acid but is less reactive than phthalanilic acid. MMX ca
lculations on phthalamic acid derivatives showed that phthalanilic aci
d has the closest distance for a most efficient intramolecular catalys
is. Additives such as cyclodextrin or metal ion do not affect the kine
tics of the reaction.