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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 23, Number 5
BKCSDE 23(5)
May 20, 2002

Title	Kinetics and Mechanism of the Pyridinolysis of Aryl Cyclobutanecarboxylates in Acetonitrile
Author	Han Joong Koh, Kwang Lae Han, Hai Whang Lee, Ikchoon Lee
Keywords	Aryl cyclobutanecarboxylates, Stepwise mechanism, Zwitterionic tetrahedral intermediate, Cross-interaction constant.
Abstract	Kinetic studies of the reaction of Z-aryl cyclobutanecarboxylates with X-pyridines in acetonitrile at 55.0℃ have been carried out. The reaction proceeds by a stepwise mechanism in which the rate-determining step is the breakdown of the zwitterionic tetrahedral intermediate, T ^± . These mechanistic conclusions are drawn based on (i) the large magnitude of ρ_X and ρ_Z, (ⅱ) the positive sign of ρ_XZ and the larger magnitude of ρ_XZ than normal S_N2 processes, (ⅲ) a small positive enthalpy of activation, ΔH ^≠, and a large negative, ΔS^≠ , and lastly (iv) adherence to the reactivity-selectivity principle (RSP) in all cases.
Page	715 - 720
Full Text	PDF

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