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Direct Chiral Resolution of Phenylalkylamines Using a Crown Ether Chiral Stationary Phase
Author(s) -
AboulEnein Hassan Y.,
Serignese Vince
Publication year - 1997
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/(sici)1099-0801(199701)11:1<7::aid-bmc607>3.0.co;2-f
Subject(s) - chemistry , chiral stationary phase , resolution (logic) , chromatography , crown ether , phase (matter) , stationary phase , chiral derivatizing agent , ether , enantiomer , stereochemistry , organic chemistry , chiral column chromatography , artificial intelligence , ion , computer science
A direct, isocratic high‐performance liquid chromatographic method is described for the enantiomeric resolution of a number of phenylalkylamines, namely, racemic cathinone, amphetamine, norephedrine, and norphenylephrine, without sample derivatization. The separations were achieved on an S ‐18‐crown‐6‐ether chiral stationary phase known as CR(+). The chromatographic parameters α (separation factor) and R s (resolution factor) lay within a narrow range for all compounds used in this study except for cathinone, which resulted in high α and R s values. The recognition mechanism for this column involves the interaction of the crown structure with a charged primary ammonium ion. The stereochemical structures of the compounds in this study contribute to the results obtained for the chromatographic parameters, especially in cathinone's case. This paper will discuss the recognition mechanism contributing to the high α and R s values obtained for cathinone. © 1997 by John Wiley & Sons, Ltd.