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Collect. Czech. Chem. Commun. 1999, 64, 1790-1796
https://doi.org/10.1135/cccc19991790

Application of the NT Solvent Nucleophilicity Scale to Attack at Sulfur: Solvolyses of Benzenesulfonyl Chlorides

Dennis N. Kevilla,* and Malcolm J. D'Souzab

a Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115-2862, U.S.A.
b Department of Chemistry, University of Wisconsin-Waukesha, Waukesha, WI 53188-2799, U.S.A.

Crossref Cited-by Linking

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  • Iazykov Mykyta, Rublova Ludmila, Canle L. Moisés, Santaballa J. Arturo: Solvent network at the transition state in the solvolysis of hindered sulfonyl compounds. J of Physical Organic Chem 2017, 30. <https://doi.org/10.1002/poc.3588>
  • Koh Han Joong, Kang Suk Jin: Rate and Product Studies on the Solvolyses of Allyl Chloroformate. Bulletin of the Korean Chemical Society 2012, 33, 4117. <https://doi.org/10.5012/bkcs.2012.33.12.4117>
  • Koh Han-Joong, Kang Suk-Jin, Kevill Dennis N.: Kinetic Studies of the Solvolyses of 2,2,2-Trichloro-1,1-Dimethylethyl Chloroformate. Bulletin of the Korean Chemical Society 2010, 31, 835. <https://doi.org/10.5012/bkcs.2010.31.04.835>
  • Bentley T. William, Jones Robert O., Kang Dae Ho, Koo In Sun: The SN3–SN2 spectrum. Rate constants and product selectivities for solvolyses of benzenesulfonyl chlorides in aqueous alcohols. J of Physical Organic Chem 2009, 22, 799. <https://doi.org/10.1002/poc.1522>
  • Seong Mi Hye, Kyong Jin Burm, Lee Young Hoon, Kevill Dennis N.: Corrrelation of the Specific Rates of Solvolysis of Ethyl Fluoroformate Using the Extended Grunwald-Winstein Equation. IJMS 2009, 10, 929. <https://doi.org/10.3390/ijms10030929>
  • Kinetic Studies of the Solvolyses of 4-Nitrophenyl Phenyl Thiophosphorochloridate. Bulletin of the Korean Chemical Society 2009, 30, 2413. <https://doi.org/10.5012/bkcs.2009.30.10.2413>
  • Kinetic Studies of the Solvolyses of Phenyl 4-Methylphenoxy Thiophosphinyl Chloride. Bulletin of the Korean Chemical Society 2009, 30, 2437. <https://doi.org/10.5012/bkcs.2009.30.10.2437>
  • Correlation of the Rates of Solvolyses of Benzhydryl Halides Using an Extended Grunwald-Winstein Equation. Bulletin of the Korean Chemical Society 2009, 30, 378. <https://doi.org/10.5012/bkcs.2009.30.2.378>
  • A Kinetic Study on Solvolysis of Diphenyl Thiophosphorochloridate. Bulletin of the Korean Chemical Society 2009, 30, 383. <https://doi.org/10.5012/bkcs.2009.30.2.383>
  • Kevill Dennis N., D'Souza Malcolm J.: Sixty Years of the Grunwald–Winstein Equation: Development and Recent Applications. Journal of Chemical Research 2008, 2008, 61. <https://doi.org/10.3184/030823408X293189>
  • D’Souza Malcolm J., Yaakoubd Lamia, Mlynarski Stacey L., Kevill Dennis N.: Concerted Solvent Processes for Common Sulfonyl Chloride Precursors used in the Synthesis of Sulfonamide-based Drugs. IJMS 2008, 9, 914. <https://doi.org/10.3390/ijms9050914>
  • Ryu Zoon Ha, Lee Sang Wok, D’Souza Malcolm J., Yaakoubd Lamia, Feld Samantha E., Kevill Dennis N.: Correlation of the Rates of Solvolysis of Two Arenesulfonyl Chlorides and of trans-β-Styrenesulfonyl Chloride — Precursors in the Development of New Pharmaceuticals. IJMS 2008, 9, 2639. <https://doi.org/10.3390/ijms9122639>
  • Correlation of the Rates of Solvolysis of Diphenylthiophosphinyl Chloride Using an Extended form of the Grunwald-Winstein Equation. Bulletin of the Korean Chemical Society 2008, 29, 1927. <https://doi.org/10.5012/bkcs.2008.29.10.1927>
  • Kevill Dennis N., Ryu Zoon Ha, Niedermeyer Monica A., Koyoshi Fumie, D'Souza Malcolm J.: Rate and product studies in the solvolyses of methanesulfonic anhydride and a comparison with methanesulfonyl chloride solvolyses. J of Physical Organic Chem 2007, 20, 431. <https://doi.org/10.1002/poc.1168>
  • Kevill Dennis N., Ryu Zoon Ha: Rate and Product Studies in the Solvolyses of Two Arenesulfonic Anhydrides. Journal of Chemical Research 2007, 2007, 365. <https://doi.org/10.3184/030823407X218084>
  • Bunton Clifford A.: The dependence of micellar rate effects upon reaction mechanism. Advances in Colloid and Interface Science 2006, 123-126, 333. <https://doi.org/10.1016/j.cis.2006.05.008>
  • Kevill Dennis N., Park Byoung-Chun, Park Kyoung-Ho, D'Souza Malcolm J., Yaakoubd Lamia, Mlynarski Stacey L., Kyong Jin Burm: Rate and product studies in the solvolyses of N,N-dimethylsulfamoyl and 2-propanesulfonyl chlorides. Org. Biomol. Chem. 2006, 4, 1580. <https://doi.org/10.1039/b518129a>
  • Bunton Clifford A.: Micellar charge effects as mechanistic criteria in spontaneous hydrolyses of acid chlorides. J of Physical Organic Chem 2005, 18, 115. <https://doi.org/10.1002/poc.747>
  • Kyong Jin Burm, Won Hoshik, Kevill Dennis N.: Application of the Extended Grunwald-Winstein Equation to Solvolyses of n-Propyl Chloroformate. IJMS 2005, 6, 87. <https://doi.org/10.3390/i6010087>
  • Kevill Dennis N., Miller Bronwyn: Application of the NT Solvent Nucleophilicity Scale To Attack at Phosphorus:  Solvolyses of N,N,N‘,N‘-Tetramethyldiamidophosphorochloridate. J. Org. Chem. 2002, 67, 7399. <https://doi.org/10.1021/jo020467n>
  • Bentley T. William, Ebdon David N.: Product selectivities and third‐order rate laws for solvolyses of ethyl phenylphosphonochloridate in aqueous alcohols. J of Physical Organic Chem 2001, 14, 759. <https://doi.org/10.1002/poc.425>