OPTICAL RESOLUTION OF RACEMIC COMPOUNDS ON CHIRAL STATIONARY PHASES OF MODIFIED CELLULOSE

Several alcohols having chiral centres on the chain linking phenyl and hydroxyl groups were chromatographed on a chiral stationary phase, based on cellulose tris-(3,5-dimethylphenylcarbamate) (Chiralcel-OD; OD-CSP). The mobile phases used were polar and non-polar solvents consisting of n-hexane and acetonitrile containing 2-propanol or benzene as modifier. The solutes containing hydroxyl groups were not eluted with non-polar eluents, and enentiomeric separation was less effective with eluents containing benzene. The enantiomeric elution order was not affected by changes in eluent polarity. The results suggest that the hydroxyl group was adsorbed on OD-CSP non-stereoselectively and that the phenyl group plays an essential part in the chiral recognition of solutes by OD-CSP. With both polar and non-polar eluents the solutes are oriented toward OD-CSP in a similar conformation. © 1990.