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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 9, Number 3
March 20, 1988 

Cross interaction Constants As a Measure of the Transition State Structure (Part 2). Nucleophilic Substitution Reactions of Phenacyl Bromides with Aniline in Methanol-Acetonitrile Mixtures
Ikchoon Lee*, In Chul Kim
Kinetics and mechanism of the nucleophilic substitution reactions of phenacyl bromides with anilines in methanol-acetonitrile mixtures at 45.0℃ are reported. The reaction is found to proceed via SN2 process, but the magnitudes of cross interaction constants, ρXY, between substituents X in the nucleophile and Y in substrate were unusually small, even after allowing for the fall off due to non-conjugative intervening -CO group in the reactant. As in the other phenacyl derivatives, the resonance shunt phenomenon was invoked to explain the remarkable diminuation of the |ρXY| values.
133 - 135
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