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

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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 - 1989

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Alkalinity
Static Electricity
Amines
Electrostatics
amines
electrostatics
aqueous solutions
Molecular Conformation
Drug Design
Biomolecules
Aniline
predictions
aniline
Pyridine
Conformations
Hydrogen
pyridines
Hydrogen bonds
drugs
Nitrogen

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

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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.",
author = "P. Nagy and K. Tak{\'a}cs-Nov{\'a}k and G. Sz{\'a}sz",
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AU - Takács-Novák, K.

AU - Szász, G.

PY - 1989

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AB - 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.

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