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Absolute pK(a) determinations for substituted phenols.

Matthew D Liptak1, Kevin C Gross, Paul G Seybold

  • 1Department of Chemistry, Hamilton College, 198 College Hill Road, Clinton, New York 13323, USA.

Journal of the American Chemical Society
|May 30, 2002
PubMed
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This study accurately predicts phenol acidity (pK(a)) using computational chemistry. Optimized structures in solution are crucial for precise calculations, benefiting the chemical community.

Area of Science:

  • Computational Chemistry
  • Physical Chemistry
  • Quantum Chemistry

Background:

  • Predicting the acidity of phenols (pK(a) values) is essential for various chemical applications.
  • Accurate computational methods are needed to determine pK(a) values without experimental fitting.

Purpose of the Study:

  • To accurately calculate the absolute pK(a) values for 20 phenols using a well-defined computational approach.
  • To assess the impact of solvation models on the accuracy of pK(a) predictions.

Main Methods:

  • Utilized the CBS-QB3 method for gas-phase free energy calculations.
  • Employed the CPCM continuum solvation model for both phenols and their anions.
  • Performed optimizations in both gas and solvent phases.

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Main Results:

  • Achieved high accuracy with standard deviations and RMSE below 0.4 pK(a) units.
  • Demonstrated that solvated phase optimized structures are critical for accurate anion calculations.
  • The study represents a highly accurate absolute determination of phenol pK(a) values.

Conclusions:

  • Accurate prediction of pK(a) values is achievable with a coherent computational strategy.
  • Solvation effects, particularly for anions, significantly influence pK(a) calculations.
  • This method provides a reliable, non-empirical approach for determining compound acidity.