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Quantitative Prediction of Solvation Free Energy in Octanol of Organic Compounds
Theoretical and Computational Chemistry Group (QTC), Faculty of Chemical Sciences, Casilla 160-C, Universidad de Concepción, Concepción, Chile
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Received: 9 February 2009; in revised form: 5 March 2009 / Accepted: 9 March 2009 / Published: 11 March 2009
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 non-halogenated alkanes, alkenes, alkynes, aromatics, alcohols, aldehydes, ketones, amines, ethers and esters; covering a ΔGS0 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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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.
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.
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.