Molecular Recognition of Acyclic Stereoisomer Using a Simple High Performance Liquid Chromatography. II

Abstract

Abstract Chromatographic separation of acyclic stereoisomers of p-substituted alcohols in a reversed phase mode was studied. Conventional C18 and C8 stationary phases and a specially designed 2-(l-pyrenyl)ethylsilylated silica gels (PYE stationary phase) were utilized for the separations. Since the β-substituted alcohols involve a hydroxy group and a hydrophilic functional group at β position to the hydroxy group, these possess a relatively tight intramolecular hydrogen bonding between these two hydrophilic functional groups to afford relatively fixed gauche conformation even in a aqueous mobile phase. In most cases, these diastereomeric β-substituted alcohols were resolved better on PYE stationary phase than on C18 and C8 stationary phases. The elution order between erythro and threo isomers was inconsistent on C18 and C8 stationary phases, when hydrophobic alkyl substituents were changed, on the other hand, threo isomer which was in more hydrophobic conformation was eluted faster on PYE phase when pheny...