Stereochemical Investigation of Cyclohexane and Terpene Compounds by Gas Chromatography

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Abstract
In GC, according to Kovats, there is a correlation between the retention increment—which is defined as the difference between retention indices obtained on a polar and a nonpolar column—and the structure of the solute. This relation was used in the structural investigation of cyclohexane compounds. The retention increments of the alkyl, hydroxyl and carbonyl functional groups were calculated from the retention indices of 32 cyclohexane compounds. Also, the retention increments arising from the spatial position of the groups and their relative positions on the ring were obtained. By comparison between the calculated and measured molecular increments of 14 terpene derivatives it could be confirmed that the retention increments are additive. Taking advantage of this evidence, the configuration of several α-and β-p-menthanediols was determined.

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