Chromatographic separation of phenylpropanol enantiomers on a quinidine carbamate-type chiral stationary phase.
The retention and the separation of the enantiomers of 1-phenylpropanol (1PP), 2-phenylpropanol (2PP), and 3-chloro-1-phenylpropanol (3CPP) on silica-bonded quinidine carbamate under normal phase HPLC conditions were investigated. A relatively high selectivity of the stationary phase for 3CPP and 1PP (alpha approximately 1.07-1.09) was achieved with eluents containing ethyl acetate as the polar modifier. These mobile phases were examined in detail. Based on the set of chromatographic and thermodynamic data collected, conclusions regarding the mechanism of enantioselectivity and the structure of the selector chiral center are made.
Asnin
Leonid
L
Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600, USA.
Guiochon
Georges
G
D000085:Acetates / Q000032:analysis; D000327:Adsorption; D002219:Carbamates / Q000737:chemistry*; D002853:Chromatography, Liquid / Q000295:instrumentation*; D019277:Entropy; D006813:Humidity; D006843:Hydrocarbons, Chlorinated / Q000302:isolation & purification; D020005:Propanols / Q000737:chemistry* / Q000302:isolation & purification*; D011802:Quinidine / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism; D013816:Thermodynamics
C507643:3-chloro-1-phenylpropanol; D000085:Acetates; D002219:Carbamates; D006843:Hydrocarbons, Chlorinated; D020005:Propanols; D012997:Solvents; C439395:1-phenylpropanol; C007650:ethyl acetate; D011802:Quinidine