Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Isotopic Acyl Exchange. I. Kinetics and Mechanism of Acyl Exchange Reaction of p-Nitrophenyl Acetate.
Yukio AkahoriSeigo Fukushima
Author information
JOURNAL FREE ACCESS

1964 Volume 12 Issue 2 Pages 166-175

Details
Abstract
Kinetic study of isotope exchange reaction between p-nitrophenyl acetate and acetic anhydride in pyridine showed that one half of the radioactivity of acetic anhydride was employed for the exchange reaction. The result agreed with that of exchange reaction between acetic acid and p-nitrophenyl acetate, and the reaction showed exact linearity of log (1-F) vs. t. The exchange rate N was shown to be the first order function with respect to the ester and the acid. From the experiments carried out at 45.0°, 37.0°, 25.5°, and 0°, 14.7 kcal./mole was estimated for Ea. The mechanism, nucleophilic attack of acetoxyl group to the positive center of carbonyl group in the ester followed by acyloxygen fission, was considered to be most probable.
Content from these authors
© The Pharmaceutical Society of Japan
Previous article Next article
feedback
Top