Theoretical calculations on the basicity of amines. Part 1. The use of molecular electrostatic potential for pKa prediction

P. Nagy, K. Novak, G. Szasz

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Abstract

Good linear correlations (r = 0.903 - 0.974) were found between the pKa, of nitrogen bases (pyridine-, aniline-derivatives, aliphatic amines) measured in aqueous solution and the minimum of the molecular electrostatic potential. The prediction of pKa for different types of amines seems possible with an accuracy of ~ 0.5 units. Using bond-increment potential calculations the estimation can be applied even for biomolecules being related to drug design. Correct consideration of both the molecular conformations and formation of the hydrogen-bonds in aqueous solutions is a prerequisite in obtaining reliable pKa values.

Original languageEnglish
Pages (from-to)257-270
Number of pages14
JournalJournal of Molecular Structure: THEOCHEM
Volume201
Issue numberC
DOIs
Publication statusPublished - Nov 1989

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ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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