Improved prediction of octanol-water partition coefficients from liquid-solute water solubilities and molar volumes

Cary T. Chiou, David W. Schmedding, Milton Manes

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

A volume-fraction-based solvent-water partition model for dilute solutes, in which the partition coefficient shows a dependence on solute molar volume (V̄), is adapted to predict the octanol-water partition coefficient (K ow) from the liquid or supercooled-liquid solute water solubility (Sw), or vice versa. The established correlation is tested for a wide range of industrial compounds and pesticides (e.g., halogenated aliphatic hydrocarbons, alkylbenzenes, halogenated benzenes, ethers, esters, PAHs, PCBs, organochlorines, organophosphates, carbamates, and amidesureas-triazines), which comprise a total of 215 test compounds spanning about 10 orders of magnitude in Sw and 8.5 orders of magnitude in Kow. Except for phenols and alcohols, which require special considerations of the Kow data, the correlation predicts the Kow within 0.1 log units for most compounds, much independent of the compound type or the magnitude in K ow. With reliable Sw and V data for compounds of interest, the correlation provides an effective means for either predicting the unavailable log Kow values or verifying the reliability of the reported log Kow data.

Original languageEnglish
Pages (from-to)8840-8846
Number of pages7
JournalEnvironmental Science and Technology
Volume39
Issue number22
DOIs
Publication statusPublished - 2005 Nov 15

Fingerprint

Octanols
partition coefficient
Density (specific gravity)
solute
solubility
Solubility
liquid
Water
Liquids
prediction
water
halogenated hydrocarbon
Triazines
Ethers
Carbamates
carbamate (ester)
aliphatic hydrocarbon
Organophosphates
Phenols
triazine

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Environmental Chemistry

Cite this

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abstract = "A volume-fraction-based solvent-water partition model for dilute solutes, in which the partition coefficient shows a dependence on solute molar volume (V̄), is adapted to predict the octanol-water partition coefficient (K ow) from the liquid or supercooled-liquid solute water solubility (Sw), or vice versa. The established correlation is tested for a wide range of industrial compounds and pesticides (e.g., halogenated aliphatic hydrocarbons, alkylbenzenes, halogenated benzenes, ethers, esters, PAHs, PCBs, organochlorines, organophosphates, carbamates, and amidesureas-triazines), which comprise a total of 215 test compounds spanning about 10 orders of magnitude in Sw and 8.5 orders of magnitude in Kow. Except for phenols and alcohols, which require special considerations of the Kow data, the correlation predicts the Kow within 0.1 log units for most compounds, much independent of the compound type or the magnitude in K ow. With reliable Sw and V data for compounds of interest, the correlation provides an effective means for either predicting the unavailable log Kow values or verifying the reliability of the reported log Kow data.",
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Improved prediction of octanol-water partition coefficients from liquid-solute water solubilities and molar volumes. / Chiou, Cary T.; Schmedding, David W.; Manes, Milton.

In: Environmental Science and Technology, Vol. 39, No. 22, 15.11.2005, p. 8840-8846.

Research output: Contribution to journalArticle

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