Improved enantiomeric separation of dihydrodiols of polycyclic aromatic hydrocarbons on chiral stationary phases by derivatization to O-methyl ethers.
K-region trans-dihydrodiol derivatives of phenanthrene, 1-methylphenanthrene, 4,5-methylenephenanthrene, pyrene, 1-bromopyrene, chrysene, benzo[c]phenanthrene, benz[a]anthracene, 1-, 4-, 6-, 7-, 11- and 12-methylbenz[a]anthracenes, 7,12-dimethylbenz[a]anthracene, 3-methylcholanthrene, and benzo[a]pyrene, and non-K-region trans-3,4-dihydrodiols of benz[a]anthracene, chrysene, and 7,12-dimethylbenz[a]anthracene are converted to O-methyl ethers. Enantiomers of these O-methyl ethers are generally more efficiently separated on Pirkle's chiral stationary phases than the enantiomers of underivatized dihydrodiols. O-Methyl ethers are substantially less polar than dihydrodiols, and O-methyl ethers are eluted with shorter retention times. Eluents of lower polarity can hence be used. This enhances chiral interactions between chiral stationary phase and solutes, allowing improved separation of enantiomers.
Yang
S K
SK
Department of Pharmacology, F. Edward Hébert School of Medicine, Uniformed Services University of the Health Sciences, Bethesda, MD 20814-4799.
Mushtaq
M
M
Bao
Z P
ZP
Weems
H B
HB
Shou
M G
MG
Lu
X L
XL
D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D008738:Methyl Ethers; D008745:Methylation; D011083:Polycyclic Compounds / Q000032:analysis*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D008738:Methyl Ethers; D011083:Polycyclic Compounds