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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 2
BKCSDE 30(2)
February 20, 2009 

Correlation of the Rates of Solvolyses of Benzhydryl Halides Using an Extended Grunwald-Winstein Equation
Han Joong Koh*, Suk Jin Kang, Cheol Ju Kim
Benzhydryl halides, Extended Grunwald-Winstein equation, SN2 pathway
Rates of solvolyses of benzhydryl chloride (Ph2CHCl, 1) and benzhydryl bromide (Ph2CHBr, 2) in ethanol, methanol, and aqueous binary mixtures incorporating ethanol, methanol, 2,2,2-trifluoroethanol (TFE) and acetone are reported. Solvolyses were also carried out in TFE-ethanol mixtures. Application of the extended Grunwald- Winstein equation led to l value of 1.19 (1), 1.29 (2) and m value of 1.00 (1), 0.77 (2), correlation coefficient of 0.965 (1) and 0.970 (2). Sensitivities (l = 1.19 (1), 1.29 (2) and m = 1.00 (1), 0.77 (2)) were similar to those obtained for several previously studied solvolyses, in which an SN2 pathway is proposed for the solvolyses of benzhydryl halides (Ph2CHX, X = Cl or Br).
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