Stereoelectronic model to explain the resolution of enantiomeric ibuprofen amides on the Pirkle chiral stationary phase.
A chiral recognition model is proposed which incorporates the electronic and steric interactions between amide derivatives of ibuprofen and the (R)-N-(3,5-dinitrobenzoyl)phenylglycine-derived Pirkle chiral stationary phase during high-performance liquid chromatography. Based on this rationale, amide derivatives of ibuprofen were prepared using 4-chloroaniline, 4-bromoaniline, aniline, 4-methoxyaniline and 1-aminonaphthylene to improve the enantiomer separation over previously reported results with this column. The amides prepared gave separation values of 1.16, 1.16, 1.19, 1.21 and 1.23, respectively. These high separation values are consistent with the proposed model.
Nicoll-Griffith
D A
DA
Department of Pharmacology, University of Toronto, Ontario, Canada.
D000577:Amides / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D007052:Ibuprofen / Q000302:isolation & purification*; D008956:Models, Chemical; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000577:Amides; D007052:Ibuprofen