Modelling the correlation between molecular electrostatic potential and pKa on sets of carboxylic acids, phenols and anilines

Authors

  • Miha Virant Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia
  • Sara Drvarič Talian National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia
  • Črtomir Podlipnik Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia
  • Barbara Hribar-Lee Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia

DOI:

https://doi.org/10.17344/acsi.2016.2962

Keywords:

molecular electrostatic potential, pKa, quantum mechanical calculations, multivariable linear regression

Abstract

Calculations of molecular electrostatic potential were correlated with experimental pKa values for different sets of acidic molecules (carboxylic acids, phenols, and anilines) to obtain linear relationships of variable quality. A single tri-parameter model function was constructed to describe the pKa dependence on MEP maxima together with two automatically generated molecular descriptors, namely the counts of carboxylic acid and amine functional groups.

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Published

02.09.2017

Issue

Vol. 64 No. 3 (2017)

Section

Physical chemistry

License

Except where otherwise noted, articles in this journal are published under the Creative Commons Attribution 4.0 International License