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KMID : 1059519940380080562
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Journal of the Korean Chemical Society
1994 Volume.38 No. 8 p.562 ~ p.569
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Effect of Substituted Groups on the Retention of Monosubstituted Phenols in Reversed-Phase Liquid Chromatography
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Kim Hoon-Joo
Lee In-Ho
Lee Dae-Woon
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Abstract
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The retention data of twenty one monosubstituted phenols in the eluent systems containing 30∼70% of methanol or acetonitrile as organic modifiers, on C18 and Phenyl columns were collected to investigate the effect of the substituted groups on the retention of phenols. The capacity factors of the solutes except amino phenols are greater on C18 than on Phenyl column. And all the solutes have shown greater capacity factors in methanol-water than that in acetonitrile-water as a mobile phase. Generally the elution order between meta and para isomers of monosubstituted phenols in consistent (p < m) regardless of the polarity of the substituted group. But the elution order between ortho and meta isomers of phenol varies with regard to the polarity of the substituted group. The retention of the monosubstituted phenols has been influenced by the interaction between the solute and unreacted silanol of columns as well as the interaction between the solute and C18 or phenyl group of columns. And then, the effect of unreacted silanol on the retention of the monosubstituted phenols is greater on C18 than on Phenyl column. And the greater hydrogen bonding acceptor basicity(β) of the substituted group is, the greater this effect is. The relationship between the retention of the monosubstituted phenols and their parameters such as van der Waals volume(VWV) and hydrogen bonding acceptor basicity(β) has been investigated. The good linearity has been observed in the plot log k' vs. (1.01VWV/100-1.84β). In consequence, the retention of the monosubstituted phenols on C18 and Phenyl columns can be easily predicted by the parameter (1.01VWV/100-1.84β).
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