Gel chromatographic behaviour of mononuclear aromatic hydrocarbons and phenols

Abstract

The gel chromatographic behaviour of aromatic hydrocarbons and phenols during elution with tetrahydrofuran in colunns packed with styrene-divinylbenzene copolymer was investigated. From the elution volumes of 27 aromatic hydrocarbons and 80 phenols, conclusions were drawn about the effects of the types and positions of substituents and of the numbers and positions of phenolic hydroxyl groups on the elution volumes of these compounds in the system under investigation. The effects of the size of the alkyl substituents and of their positions with respect to the hydroxyl group of phenols were demonstrated, and the partial contributions of the alkyl and hydroxyl groups to the elution volumes were calculated. Chromatographic results were used for the characterization of the solvatability of phenolic molecules with tetrahydrofuran and as the basis of a discussion of problems of the steric hindrance of hydroxyl groups due to neighbouring substituents.