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Int. J. Mol. Sci. 2008, 9(12), 2639-2657; doi:10.3390/ijms9122639

Correlation of the Rates of Solvolysis of Two Arenesulfonyl Chlorides and of trans-β-Styrenesulfonyl Chloride — Precursors in the Development of New Pharmaceuticals

1
Department of Chemistry, Dong-Eui University, 24 Kaya-dong, Busan-Jin-Gu, Busan 614-714, Korea
2
Department of Chemistry, Wesley College, 120 N. State Street, Dover, Delaware 19901-3875, USA
3
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115- 2862, USA
*
Authors to whom correspondence should be addressed.
Received: 21 November 2008 / Revised: 16 December 2008 / Accepted: 17 December 2008 / Published: 17 December 2008
(This article belongs to the Special Issue Grunwald-Winstein Equations – 60 Years & Counting)
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Abstract

Additional specific rates of solvolysis have been determined, mainly in fluoroalcohol containing solvents, for benzenesulfonyl chloride (1) and p-nitrobenzenesulfonyl chloride (2). For trans-β-styrenesulfonyl chloride (3), a study has been carried out in 43 pure and binary solvents, covering a wide range of hyroxylic solvent systems. For the specific rates of solvolyses of each of the three substrates, a good correlation was obtained over the full range of solvents when the extended Grunwald-Winstein equation was applied. The sensitivities to changes in solvent nucleophilicity and solvent ionizing power are similar to values determined earlier and an SN2 process is proposed. For 3, kinetic solvent isotope effects of 1.46 for kH2O/kD2O and 1.76 for kMeOH/kMeOD were determined. These are also compared to literature values for other sulfonyl chlorides. View Full-Text
Keywords: Solvolysis; sulfonyl transfer; benzenesulfonyl chloride; paranitrobenzenesulfonyl chloride; trans-β-styrenesulfonyl chloride; Grunwald-Winstein equation; Linear Free Energy Relationships; kinetic solvent isotope effect; general base catalysis Solvolysis; sulfonyl transfer; benzenesulfonyl chloride; paranitrobenzenesulfonyl chloride; trans-β-styrenesulfonyl chloride; Grunwald-Winstein equation; Linear Free Energy Relationships; kinetic solvent isotope effect; general base catalysis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Ryu, Z.H.; Lee, S.W.; D’Souza, M.J.; Yaakoubd, L.; Feld, S.E.; Kevill, D.N. Correlation of the Rates of Solvolysis of Two Arenesulfonyl Chlorides and of trans-β-Styrenesulfonyl Chloride — Precursors in the Development of New Pharmaceuticals. Int. J. Mol. Sci. 2008, 9, 2639-2657.

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