Chapter 7. Carbon acidity resulting from sulfur substituents

  1. Saul Patai and
  2. Zvi Rappoport
  1. Gernot Boche1,
  2. John C. W. Lohrenz1,
  3. Jerzy Cioslowski2 and
  4. Wolfram Koch3,†

Published Online: 16 JAN 2010

DOI: 10.1002/9780470034408.ch7

Sulphur-Containing Functional Groups (1993)

Sulphur-Containing Functional Groups (1993)

How to Cite

Boche, G., Lohrenz, J. C. W., Cioslowski, J. and Koch, W. (1993) Carbon acidity resulting from sulfur substituents, in Sulphur-Containing Functional Groups (1993) (eds S. Patai and Z. Rappoport), John Wiley & Sons, Inc., Chichester, UK. doi: 10.1002/9780470034408.ch7

Editor Information

  1. The Hebrew University, Jerusalem

Author Information

  1. 1

    Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, D-3550 Marburg, Germany

  2. 2

    Department of Chemistry, The Florida State University, Tallahassee, Florida 32306–3006, USA

  3. 3

    Institut für Supercomputing und Angewandte Mathematik, Wissenschaftliches Zentrum, IBM Deutschland GmbH, Tiergartenstr. 15, D-6900 Heidelberg, Germany

  1. Institut für Organische Chemie, Technische Universität Berlin, Strasse des 17. Juni 135, D-1000 Berlin 12, Germany

Publication History

  1. Published Online: 16 JAN 2010
  2. Published Print: 30 SEP 1993

ISBN Information

Print ISBN: 9780471930464

Online ISBN: 9780470034408



  • sulfonium ions;
  • conjugative stabilization;
  • negative hyperconjugation;
  • organosodium compounds;
  • nonbonded interactions


This chapter contains sections titled:

  • Introduction

  • The Stabilization of a Negative Charge by the —SH(R) Group: Model Calculations and Experimental Results

  • The Stabilization of a Negative Charge by the —SH(R) and the —OH(R) Groups: A Comparison of Theoretical and Experimental Results

  • The Carbon Acidity of Thioethers, Sulfoxides, Sulfones and Sulfonium Ions: A Comparative Analysis on the Basis of Theory and Experiment

  • Appendix

  • References