JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 69 No 2 (2024): Journal of the Chilean Chemical Society
Original Research Papers

DETERMINATION OF pKa AND pKb FROM ELECTRONIC PROPERTIES DERIVED FROM CONCEPTUAL DENSITY FUNCTIONAL THEORY (cDFT)

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  • José Muñoz - Espinoza,
  • Germán Barriga-González,
  • Sergio Jiménez-Meza
José Muñoz - Espinoza
Universidad de Chile
Germán Barriga-González
Metropolitan University of Educational Sciences
Published January 10, 2025
Keywords
  • Acidity,
  • Basicity,
  • Nucleophilicity,
  • Electrophilicity,
  • Multilinear Correlation
How to Cite
Muñoz - Espinoza, J., Barriga-González, G., & Jiménez-Meza, S. (2025). DETERMINATION OF pKa AND pKb FROM ELECTRONIC PROPERTIES DERIVED FROM CONCEPTUAL DENSITY FUNCTIONAL THEORY (cDFT). Journal of the Chilean Chemical Society, 69(2), 6104-6109. Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/2645

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Abstract

In the present work we apply a semiempirical method capable of calculating the pka and pkb values of a series of organic acids and bases through their electronic properties. This multilinear model, analogous to the one introduced by Kamlet-Taft, relates acid-base properties such as HBA and HBD to the regional electrophilicity and nucleophilicity derived from cDFT. To test the model, it was applied to a series of mono and dicarboxylic acids, as well as aliphatic/cyclic and heterocyclic amines, showing us that the model is only functional when the series of compounds present similar characteristics such as functional groups. Based on the regionalization of the electrophilicity and nucleophilicity, it can be observed that the acid-base characteristics are not exclusive to limited regions of the molecules, but that these present a bifunctional character that shifts to the relative characteristics of acid and/or base according to the global distribution of the electronic density.

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