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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 10
BKCSDE 29(10)
October 20, 2008

Title	Correlation of the Rates of Solvolysis of Diphenylthiophosphinyl Chloride Using an Extended form of the Grunwald-Winstein Equation
Author	Han Joong Koh*, Suk Jin Kang, Dennis N Kevill
Keywords	Diphenylthiophosphinyl chloride, Extended Grunwald-Winstein equation, SN2 pathway
Abstract	Rate of solvolysis of diphenylthiophosphinyl chloride in ethanol, methanol, and aqueous binary mixtures incorporating ethanol, methanol, acetone, 2,2,2-trifluoroethanol (TFE) or 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) are reported. Solvolyses were also carried out in TFE-ethanol mixtures. For five representative solvents, studies were made at several temperatures and activation parameters determined. The 29 solvents gave a reasonably precise extended Grunwald-Winstein equation plot, correlation coefficient (R) of 0.933, which improved to 0.983 when the four TFE-ethanol points were excluded. The sensitivities (l = 1.00 and m = 0.64) were similar to those obtained for dimethyl phosphorochloridate and phosphorochloridothionate and diphenylphosphinyl chloride (1). As with the four previously studied solvolyses, an SN2 pathway is proposed for the solvolyses of diphenylthiophosphinyl chloride. The activation parameters, ΔH≠ and ΔS≠, were determined and they are also in line with values expected for an SN2 reaction.
Page	1927 - 1931
Full Text	PDF

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