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Analysis and prediction of hydrophobicity parameters of substituted acetanilides, benzamides and related aromatic compounds
Author(s) -
Nakagawa Yoshiaki,
Izumi Keiichi,
Oikawa Nobuhiro,
Sotomatsu Tomoko,
Shigemura Masao,
Fujita Toshio
Publication year - 1992
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1002/etc.5620110704
Subject(s) - acetanilide , partition coefficient , chemistry , quantitative structure–activity relationship , solvation , steric effects , nitrobenzene , benzene , lipophilicity , substituent , benzene derivatives , free energy relationship , taft equation , computational chemistry , octanol , hydrogen bond , organic chemistry , stereochemistry , molecule , chemical synthesis , kinetics , reaction rate constant , biochemistry , physics , quantum mechanics , in vitro , catalysis
The partition coefficient P in the 1‐octanol/water system was analyzed for a great number of multisubstituted benzenes of ecotoxicological importance consisting of acetanilides, benzamides, nitrobenzenes, and anisoles having various substitution patterns in terms of the Δ log P (log P – log P [unsubstituted benzene]) quantitatively with free energy‐related physicochemical substituent parameters. The analyses showed that the stereoelectronic effects of ortho, meta, and para substituents on the relative solvation of individual polar groups capable of hydrogen bonding with the partitioning solvents are very important in determining the variations in the log P value. The effects were additive in the set of complicated multisubstituted benzenes, leading to a correlation equation represented by a linear combination of terms of hydrophobic, electronic, and steric parameters summed up over substituents. It was suggested that the procedure be extended to analyze and predict the log P value of any multiply substituted benzenes.