Chiral microemulsion electrokinetic chromatography: Effect of cosurfactant identity on enantioselectivity, methylene selectivity, resolution, and other chromatographic figures of merit.
The effect of cosurfactant identity on microemulsion size, elution range, retention factor, enantioselectivity, methylene selectivity, efficiency, and resolution in chiral microemulsion formulations was examined. The chiral surfactant dodecoxycarbonylvaline was used in conjunction with the cosurfactants 1-butanol, 1-pentanol, 2-pentanol, 1-hexanol, 2-hexanol, cyclopentanol, and cyclohexanol. The millimolar concentration of cosurfactant was held constant regardless of identity. Ethyl acetate was incorporated as the microemulsion oil core and the buffer utilized was 50 mM phosphate at a pH of 7.0. In general, secondary alcohols improved enantioselectivities and primary alcohols had the opposite effect, with the exception of the 1-butanol. The trends observed varied slightly depending on analyte. Of the six chiral analytes tested, cyclopentanol provided the best enantioselectivity for three, 1-butanol for two compounds, and 2-pentanol for one analyte. The lowest enantioselectivities were achieved with 1-pentanol or 1-hexanol for all compounds. Methylene selectivity was found to decrease with reductions in alcohol chain length. Among equal carbon number alcohols, methylene selectivity was lower for secondary alcohols. Efficiency and resolution values varied with different cosurfactants and depended on analyte identity.
Kahle
Kimberly A
KA
Department of Chemistry, Drexel University, Philadelphia, PA 19104, USA.
Foley
Joe P
JP
D000085:Acetates / Q000737:chemistry; D053801:Capillary Electrochromatography / Q000379:methods*; D004655:Emulsions; D004809:Ephedrine / Q000031:analogs & derivatives* / Q000302:isolation & purification; D005233:Fatty Alcohols / Q000737:chemistry*; D010316:Particle Size; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry*; D014633:Valine / Q000031:analogs & derivatives* / Q000737:chemistry
D000085:Acetates; D004655:Emulsions; D005233:Fatty Alcohols; D013501:Surface-Active Agents; C104188:N-dodecoxycarbonylvaline; C041707:N-methylephedrine; C007650:ethyl acetate; D004809:Ephedrine; D014633:Valine