Article

Estimation of pKa for organic oxyacids using calculated atomic charges

  1. Steven L. Dixon,
  2. Peter C. Jurs*

Article first published online: 7 SEP 2004

DOI: 10.1002/jcc.540141208

Issue

Journal of Computational Chemistry

Journal of Computational Chemistry

Volume 14, Issue 12, pages 1460–1467, December 1993

Additional Information

How to Cite

Dixon, S. L. and Jurs, P. C. (1993), Estimation of pKa for organic oxyacids using calculated atomic charges. Journal of Computational Chemistry, 14: 1460–1467. doi: 10.1002/jcc.540141208

Author Information

  1. Department of Chemistry, The Pennyslvania State University, University Park, Pennsylvania 16802

*Department of Chemistry, The Pennyslvania State University, University Park, Pennsylvania 16802

Publication History

  1. Issue published online: 7 SEP 2004
  2. Article first published online: 7 SEP 2004
  3. Manuscript Accepted: 18 JUN 1993
  4. Manuscript Received: 11 FEB 1993

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Abstract

A method for the estimation of pKa from empirically calculated atomic charges has been developed and tested on a diverse set of organic oxyacids. The approach involves a comparison of the atomic charges calculated for both the acid and the negative ion that is formed after loss of the acidic proton. These charges have been used in conjunction with the familiar concepts of induction and resonance to develop an accurate formula to predict pKa. Results for a set of 135 compounds, including alcohols, phenols, and carboxylic acids, yielded a fit of pKa with r = 0.993 and an rms error of 0.455. © John Wiley & Sons, Inc.

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