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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 13, Number 4
BKCSDE 13(4)
April 20, 1992 

Limitations of the Transition State Variation Model(5) Dual Reaction Channels for Solvolysis of Dansyl Chloride
In Sun Koo, Ocg-Kyeong Lee, Ikchoon Lee*
Rate of solvolysis of dansyl chloride in aqueous binary mixtures of acetone, methanol and ethanol are reported. Kinetic solvent isotope effects in methanol and product selectivities in alcohol-water mixtures are also reported. Kinetic data are interpreted with the Grunwald-Winstein and Kivinen equations. The value of kCH3OH/kCH3OD = 1.76 suggests that a general have catalyzed and/or an SAN pathway is operative in methanol, a less polar solvent. Rate-rate profiles for solvolysis of dansyl chloride in the aqueous binary media indicate a change in reaction channel from SAN (in less polar media) to SN2 (in more polar media) mechanism.
395 - 398
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