Abstract
We investigated here the HPLC-separation of alcohols including linear and cyclic monools and diols and sugar derivatives using a silica-ODS column coated with a polyhydroxy macrocyclic host compound. The host used has polar hydroxyl groups, thereby enhancing the polarity of the surface of the column. The retention times of most alcohols on such a host-coated column (Rh) are shorter than those on a host-noncoated column (RO), as a consequence. Plots of (RORh) vs RO give a straight line for most alcohols. However, there are signficant downward deviations for such alcohols as 1-pentanol, cyclohexanol, 4-methylcyclohexanol, and hexyl α and β xylosides, in addition to cyclohexanols. This indicates that these alcohols interact with the host molecule. In particular, Rh's for 1, 2-, 1, 3-, and cis-1, 4-cyclohexanediols are slightly longer than the corresponding RO values. These results, taken in conjunction with the stereoselectivity observed, strongly suggest that there is hydrogen-bonding interaction between these diols and the host.
