Aminolysis of Y-substituted phenyl X-substituted benzoates with piperidine: effect of nonleaving group substituent.
The title reaction has been suggested to proceed through a zwitterionic tetrahedral intermediate with a change in the rate determining step on the basis of the curved Brønsted-type plots obtained. The curvature center of the curved Brønsted-type plots is at pKa = 6.4 regardless of the electronic nature of the substituent X in the benzoyl moiety.
Um
Ik-Hwan
IH
Department of Chemistry, Ewha Womans University, Seoul 120-750, Korea. ihum@ewha.ac.kr
Lee
Ji-Youn
JY
Ko
Seung-Hak
SH
Bae
Sun-Kun
SK