Abstract
Intramolecular catalyzed hydrolysis of amide bond by a second amide group was investigated in the acidic hydrolysis of 2-acylamidobenzamide as model compound. In the 2-arylamido series, the hydrolysis rate decreases as the substituent becomes more electron withdrawing. A Hammett reaction constant was found to be -1.05 and is consistent with the intramolecular catalyzed mechanism. The connection between the present results and penicillin stability in an acidic medium was discussed.
