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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 21, Number 5
BKCSDE 21(5)
May 20, 2000

Title	Theoretical Studies on Phenyl Group Migration of Protonated 1,2-Diphenyl Hydrazines
Author	Chau Kyung Kim,* In Young Lee, Chang Kon Kim, Ikchoon Lee
Keywords
Abstract	Phenyl group migration within protonated l,2-diphenyl hydrazines as been studied theoretically using the semi-empirical AM1 method. This reaction proceeds through a 3-membered cyclic transition state and requires high activation energy. ln the reactant, there was no resonance stabilization for the moving Z-ring, however,resonance stabilization between two nitrogen atoms and the Z-ring was achieved at the transition state. The Hammett pz+ values are large due to the direct involvement of the Z-ring in the reaction, and the development of a negative charge on the reaction center gives them a positive value. ln the case of the non-moving ring, ρy values are small and negative owing to the smaller positive charge increase in the reaction center. The cross-interaction constant, ρyz, was obtained from the activation enthalpies, using the multiple linear regression method, and the interaction between two substituents, Y and Z, is examined.
Page	477 - 482
Full Text	PDF

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