Hydrogen-bonding abilities for phenols assessed by quantitative analyses of their partition coefficients derived from different partitioning systems.
We recently proposed a new hydrogen-accepting scale, S(HA), on the basis of the heat of formation calculated by the conductor-like screening model (COSMO) method. In this work, the same approach was applied to a series of compounds with a common hydrogen-donor group. Thus the S(HA) values for monosubstituted phenols were calculated and used for correlating their log P(oct) values (P(oct): 1-octanol/water partition coefficient) with log P(CL) (P(CL): chloroform/water partition coefficient) and log P(E) (P(E): butyl ether/water partition coefficient). It was demonstrated that the S(HA) parameter works effectively, providing excellent correlations whose physicochemical meanings are well rationalized in terms of hydrogen-bonding characteristics of the substituents.
Yamagami
Chisako
C
Kobe Pharmaceutical University, Kobe. yamagami@kobepharma-u.ac.jp
Hamasaki
Akira
A
Kumagai
Yukiko
Y
Moritoki
Tetsuhiro
T
Tanahashi
Takao
T
D000465:Algorithms; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D006860:Hydrogen Bonding; D010636:Phenols / Q000737:chemistry*; D012995:Solubility
D010636:Phenols