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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 20, Number 12
BKCSDE 20(12)
December 20, 1999 

Nucleophilic Substitution Reaction of α-Methoxy- α-(trifluoromethyl)phenylacetyl Chloride in Alcohol-Water Mixtures
In Sun Koo, Seong In Lee, Sun Kyoung An, Kiyull Yang, Ikchoon Lee
Solvolyses of α-methoxy- α-(trifluoromethyl)phenylacetyl chloride in H2O, D2O, CH3OD, 50% D2O-CH3OD, and in aqueous binary mixtures of acetone, dioxane, ethanol and methanol are investigated at 25.0℃. The Grunwald-Winstein plots of first-order rate constants for α-methoxy- α-(trifluoromethyl)phenylacetyl chloride with YCl show a dispersion phenomenon. Solvent nucleophilicity N has been shown to give considerable im-provement when it is added as an lN term to the original Grunwald-Winstein for the solvolyses of α-methoxy- α-(trifluoromethyl)phenylacetyl chloride. The dispersions in the Grunwald-Winstein correlations in the present studies are caused by solvent nucleophilicity. The magnitude of l and m values associated with a change of solvent composition predicts the associative SN2 transition state. The kinetic solvent isotope effects determined in deuterated water and methanol are consistent with the proposed mechanism of the general base catalyzed associative SN2 or SAN mechanism for the of α-methoxy- α-(trifluoromethyl)phenylacetyl chloride.
1451 - 1456
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