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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 15, Number 7
BKCSDE 15(7)
July 20, 1994 

The Magnitude of ρX(ρnuc) versus the Extent of Bond Formation in SN2 Reactions
Ikchoon Lee*, Han Joong Koh, Byung Choon Lee, Byong Seo Park
The secondary deuterium kinetic isotope effects (SDKIE) involving deuterated aniline nucleophiles are reported for the reactions of benzyl bromides and chlorides and benzoyl chlorides in acetonitrile. The benzyl systems behave normally as to the trend of changes in SDKIE with the magnitude of ρX(ρnuc), whereas benzoyl system shows ananomaly; │ρX│ decreases with increase in the extent of bond making estimated by the SDKIE. This has been ascribed to the negative charge accumulation at the reaction center carbon in the transition state. The magnitude of ρXY is found to decrease by ca. 0.03 with ten degree rise in the reaction temperature.
576 - 581
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