Calculation of the Three Partition Coefficients logP_ow, logK_oa and logK_aw of Organic Molecules at Standard Conditions at Once by Means of a Generally Applicable Group-Additivity Method

Abstract

Assessment of the environmental impact of organic chemicals has become an important subject in chemical science. Efficient quantitative descriptors of their impact are their partition coefficients logPow, logKoa and logKaw. We present a group-additivity method that has proven its versatility for the reliable prediction of many other molecular descriptors for the calculation of the first two partition coefficients and indirectly of the third with high dependability. Based on the experimental logPow data of 3332 molecules and the experimental logKoa data of 1900 molecules at 298.15 K, the respective partition coefficients have been calculated with a cross-validated standard deviation S of only 0.42 and 0.48 log units and a goodness of fit Q2 of 0.9599 and 0.9717, respectively, in a range of ca. 17 log units for both descriptors. The third partition coefficient logKaw has been derived from the calculated values of the former two descriptors and compared with the experimentally determined logKaw value of 1937 molecules, yielding a standard deviation σ of 0.67 log units and a correlation coefficient R2 of 0.9467. This approach enabled the quick calculation of 29,462 logPow, 27,069 logKoa and 26,220 logKaw values for the more than 37,100 molecules of ChemBrain’s database available to the public.

Keywords

• group-additivity method
• Gauss–Seidel diagonalisation
• partition coefficient
• logP_ow
• logK_oa
• logK_aw