HPLC behavior and hydrophobic parameters of some anilides

Abstract

The chromatographic behavior of para substituted anilides of 2,2-dimethylpropanoic, benzoic and α-phenyl acetic acid has been studied by reversed-phase high performance liquid chromatography HPLC was performed on a C-18 column with various aqueous methanol mobile phases. The influence on the retention of anilide type and additional substituents in the molecule is discussed. Several chromatographic hydrophobicity parameters (CHP) have been calculated by linear correlation between log k of the investigated compounds and the concentration of methanol in the mobile phase. The chromatographic hydrophobicity parameters were compared with the log P values calculated by Rekker's fragmental method. The results show moderate correlations of CHP with log P. Thus, multiple linear regressions have been applied. It was found that besides log P even the electronic effects of individual polar groups capable of hydrogen bonding proved to be very important in hydrophobic characterization of the molecule.