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[摘要]：Partition coeffs. were measured for 47 compds. in the hexadecane/water (Phxd) and 1-octanol/water (Poct) systems. Some types of hydrogen bond acceptor presented by these compds. to the partitioning systems are not well represented in the literature of alkane/water partitioning. The difference, DlogP, between logPoct and logPhxd is a measure of the hydrogen bonding potential of a mol. and is identified as a target for predictive modeling. Minimized mol. electrostatic potential (Vmin) was shown to be an effective predictor of the contribution of hydrogen bond acceptors to DlogP. Carbonyl oxygen atoms were found to be stronger hydrogen bond acceptors for their electrostatic potential than heteroarom. nitrogen or oxygen bound to hypervalent sulfur or nitrogen. Values of Vmin calcd. for hydrogen-bonded complexes were used to explore polarization effects. Predicted logPhxd and DlogP were shown to be more effective than logPoct for modeling brain penetration for a data set of 18 compds. |
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