Quantitative Prediction of Solvation Free Energy in Octanol of Organic Compounds

doi:10.3390/i10031031

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Int. J. Mol. Sci. 2009, 10(3), 1031-1044; doi:10.3390/i10031031

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Quantitative Prediction of Solvation Free Energy in Octanol of Organic Compounds

Eduardo J. Delgado* and Gonzalo A. Jaña

Theoretical and Computational Chemistry Group (QTC), Faculty of Chemical Sciences, Casilla 160-C, Universidad de Concepción, Concepción, Chile

* Author to whom correspondence should be addressed.

Received: 9 February 2009; in revised form: 5 March 2009 / Accepted: 9 March 2009 / Published: 11 March 2009

(This article belongs to the Special Issue Recent Advances in QSAR/QSPR Theory)

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Abstract: The free energy of solvation, ΔG_S⁰ , 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 non-halogenated alkanes, alkenes, alkynes, aromatics, alcohols, aldehydes, ketones, amines, ethers and esters; covering a ΔG_S⁰ range from about –50 to 0 kJ·mol-1. The model predicts the free energy of solvation with a squared correlation coefficient of 0.93 and a standard deviation, 2.4 kJ·mol-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.

Keywords: QSPR; solvation free energy; octanol; organic compounds

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MDPI and ACS Style

Delgado, E.J.; Jaña, G.A. Quantitative Prediction of Solvation Free Energy in Octanol of Organic Compounds. Int. J. Mol. Sci. 2009, 10, 1031-1044.

AMA Style

Delgado EJ, Jaña GA. Quantitative Prediction of Solvation Free Energy in Octanol of Organic Compounds. International Journal of Molecular Sciences. 2009; 10(3):1031-1044.

Chicago/Turabian Style

Delgado, Eduardo J.; Jaña, Gonzalo A. 2009. "Quantitative Prediction of Solvation Free Energy in Octanol of Organic Compounds." Int. J. Mol. Sci. 10, no. 3: 1031-1044.

Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert