Direct separation of non-K-region mono-ol and diol enantiomers of phenanthrene, benz[a]anthracene, and chrysene by high-performance liquid chromatography with chiral stationary phases.
The direct separation of 26 bay region and non-bay region mono-ol and diol enantiomers of phenanthrene, benz[a]anthracene, and chrysene was compared by high-performance liquid chromatography on commercially available columns, packed with gamma-aminopropylsilanized silica to which either (R)-N-(3,5-dinitrobenzoyl)phenylglycine(R-DNBPG) or (S)-N-(3,5-dinitrobenzoyl)leucine(S-DNBL) was either ionically or covalently bonded. In general, enantiomers of bay region mono-ols and diols are more efficiently resolved than those of non-bay region derivatives. Elution orders of enantiomers on either chiral stationary phase are the same, regardless of whether the chiral stationary phase is ionically or covalently bonded. Except for the enantiomers of 4-hydroxy-4-methyl-1,2,3,4-tetrahydrobenz[a]anthracene, 1,2,3,4-tetrahydrobenz[a]anthracene trans-1,2-diol, and benz[a]anthracene trans-1,2-dihydrodiol, elution orders of resolved enantiomers on R-DNBPG are reversed on S-DNBL. The enantiomers are generally more efficiently resolved on R-DNBPG than on S-DNBL. With the exception of the elution order of the enantiomeric 4-hydroxy-1,2,3,4-tetrahydrochrysene, the results of this study are consistent with the chiral recognition mechanisms proposed by Pirkle and co-workers, who developed the chiral stationary phases used in this study.
D001551:Benz(a)Anthracenes / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid; D002911:Chrysenes / Q000302:isolation & purification*; D005998:Glycine / Q000031:analogs & derivatives* / Q000032:analysis; D007930:Leucine / Q000031:analogs & derivatives* / Q000032:analysis; D008968:Molecular Conformation; D009579:Nitrobenzoates / Q000032:analysis*; D010616:Phenanthrenes / Q000302:isolation & purification*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D001551:Benz(a)Anthracenes; D002911:Chrysenes; D009579:Nitrobenzoates; D010616:Phenanthrenes; C051871:N-(3,5-dinitrobenzoyl)phenylglycine; C051872:N-(3,5-dinitrobenzoyl)leucine; D007930:Leucine; D005998:Glycine