Hydrophobicity parameters determined by reversed-phase liquid chromatography. XVI: A new hydrogen-accepting parameter for monosubstituted thiophenes and furans for correlating retention factors and octanol-water partition coefficients.
We recently proposed a new hydrogen-accepting parameter, S(HA), for monosubstituted (di)azines on the basis of the heat of formation calculated by the conductor-like screening model (COSMO) method. In this work, S(HA) values for monosubstituted thiophenes and furans were calculated and the results were applied to the analysis of relationships between log P (P: 1-octanol/water partition coefficient) and log k (k: retention factor obtained by reversed phase HPLC). The S(HA) parameter was found to work effectively as a hydrogen-bonding parameter in a range of heteroaromatic compounds.
Yamagami
Chisako
C
Kobe Pharmaceutical University, Motoyamakita-machi, Kobe, Japan. yamagami@kobepharma-u.ac.jp
Tachikawa
Hiromi
H
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D005663:Furans / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D000442:Octanols / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry*
D005663:Furans; D000442:Octanols; D013876:Thiophenes; D006859:Hydrogen