Quantitative prediction of solvation free energy in octanol of organic compounds

Eduardo J. Delgado, Gonzalo A. Jaña

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

The free energy of solvation, ΔGs0, in octanol of organic compunds is quantitatively predicted from the molecular structure. The model, involving only three molecular descriptors, is obtained by multiple linear regression analysis from a data set of 147 compounds containing diverse organic functions, namely, halogenated and nonhalogenated alkanes, alkenes, alkynes, aromatics, alcohols, aldehydes, ketones, amines, ethers and esters; covering a ΔGs0 range from about -50 to 0 kJmol -1. The model predicts the free energy of solvation with a squared correlation coefficient of 0.93 and a standard deviation, 2.4 kJmol -1, just marginally larger than the generally accepted value of experimental uncertainty. The involved molecular descriptors have definite physical meaning corresponding to the different intermolecular interactions occurring in the bulk liquid phase. The model is validated with an external set of 36 compounds not included in the training set.

Original languageEnglish
Pages (from-to)1031-1044
Number of pages14
JournalInternational Journal of Molecular Sciences
Volume10
Issue number3
DOIs
Publication statusPublished - Mar 2009

Keywords

  • Octanol
  • Organic compounds
  • QSPR
  • Solvation free energy

ASJC Scopus subject areas

  • Catalysis
  • Molecular Biology
  • Spectroscopy
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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