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2021, Vol.94, No.7

1807-1814

A Practical Prediction of LogPo/w through Semiempirical Electronic Structure Calculations with Dielectric Continuum Model

Teruyuki Takahashi ,*1Toru Matsui ,2Kowit Hengphasatporn ,3 and Yasuteru Shigeta *3
1Department of Physics, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Ibaraki 305-8571, Japan
2Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Ibaraki 305-8571, Japan
3Center for Computational Sciences, University of Tsukuba, 1-1-1 Tennodai, Ibaraki 305-8571, Japan
https://doi.org/10.1246/bcsj.20210035

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Abstract

We examined various combinations of semiempirical and polarizable continuum methods and found that SMD/PM7 provides the highest accuracy in calculating LogPo/w. The correlation between the experimental and calculated LogPo/w is approximately R2 = 0.74. However, this result is not sufficiently accurate for achieving a practical prediction. To clarify the details of the calculation results, a linear fitting was conducted for each functional group and each atom. The results showed a large variation, indicating a large error. We then conducted a multiple regression analysis using the number of atoms in the molecule, the number of multiple bonds, the ring structure, and the indicator for aromatic nature as explanatory variables and the experimental value of LogPo/w as the objective variable; finally, we incorporated a correction to the calculated value of LogPo/w. We showed that the accuracy was significantly improved to approximately R2 = 0.95 when adopting the difference in solvation energy, along with four additional explanatory variables.

figure

Using the combinations of the semiempirical quantum chemical method and the polarizable continuum model, LogPo/w values are evaluated. Using the calculation data and several explanatory variables, the multiple regression analysis gives better correlation between the experimental and computed LogPo/w values.

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