Evaluation of three models for predicting newly determined octanol-water partition coefficients and mechanisms for substituted aromatic compounds

Water Environ Res. 2002 May-Jun;74(3):242-7. doi: 10.2175/106143002x139965.

Abstract

Octanol-water partition coefficients (K(ow)) of 27 substituted aromatic compounds, including polyhalogenated aromatics, were determined. A molecular connectivity index (MCI), a theoretical linear solvation energy relationship, and a quantum chemical method were applied to model the property and study the partition mechanism. The multiple correction coefficients (r2(adj)) (> or = 0.870) and the standard errors (< or = 0.33) for log K(ow) indicated that the models were successful. Comparing the three models, the MCI method (including the nondisperse force factor) was the most satisfactory. However, the quantum chemical model based on the potential of the negative atomic charge, total energy, and molecular weight revealed that the molecular bulk properties and electrostatic interaction were the most important factors influencing the partition process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Forecasting
  • Models, Chemical*
  • Octanols / chemistry
  • Polycyclic Aromatic Hydrocarbons / chemistry*
  • Solubility
  • Structure-Activity Relationship
  • Water / chemistry
  • Water Pollutants / analysis*

Substances

  • Octanols
  • Polycyclic Aromatic Hydrocarbons
  • Water Pollutants
  • Water