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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 16, Number 9
BKCSDE 16(9)
September 20, 1995 

Kinetics and Mechanism of Aminolysis of Phenyl Benzoates in Acetonitrile
Han Joong Koh, Ho Chan Lee, Hai Whang Lee, Ikchoon Lee
The kinetics and mechanism of the reactions of phenyl benzoates with benzylamines and pyrrolidine are investigated in acetonitrile. The variations of ρX (ρXY>0) and ρZ (ρYZ<0) with respect to the substituent in the substrate (σY) indicate that the reactions proceed through a tetrahedral intermediate, T±, with its breakdown in the rate determining step. The large magnitudes of ρZ, ρ XY and ρYZ as well as the effects of secondary kinetic isotope effects involving deuterated nucleophiles are also in line with the proposed mechanism.
839 - 844
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