Prediction of the 1-octanol/H2O partition coefficient, log P, by ab initio MO calculations: hydrogen-bonding effect of organic solutes on log P.
To predict the 1-octanol/H2O partition coefficient, log P, based on molecular structures, we calculated the solvent accessible surface area and the solvation energy difference of 166 organic molecules between 1-octanol and water environments with the ab initio molecular orbital self-consistent reaction field method, and then analyzed the relationships among the measured log P values with these two structural quantities by multiple linear-regression analyses. Physicochemically meaningful correlations were obtained, suggesting that non-hydrogen bonding and hydrogen-acceptor molecules behave similarly to each other in partitioning, but that hydrogen-donor molecules behave differently from the former molecules. The results provide a new computational approach for predicting log P.
Chuman
Hiroshi
H
Faculty of Pharmaceutical Sciences, The University of Tokushima, Japan. hchuman@ph.tokushima-u.ac.jp
Mori
Atsushi
A
Tanaka
Hideji
H