Preparation and chiral recognition of a mono[6A-N-1-(2-hydroxy)-phenylethylimino-6A-deoxy]-beta-cyclodextrin HPLC stationary phase.
A novel chiral stationary phase (CSP) is obtained by linking the beta-CD to a chiral block (commercially available phenylglycinol) by rigid C=N bond. This chiral stationary phase exhibites good enantioselectivity for several alkylaromatic alcohols and a variety of ferrocene derivatives under reversed-phase conditions, with the best Rs value achieve up to 6.19. The hydrogen bonding interaction may be the primary factor, also pi-pi interaction or dipole-dipole interaction has some effect on chiral separation. The dependence of the natural logarithms of retention and selectivity factors (lnk' and lnalpha) on the inverse of temperature 1/T (van't Hoff plots) is used to determine thermodynamic data referring to the separation of the enantiomers. Calculated thermodynamic constants Delta(DeltaH degrees ), Delta (DeltaS degrees ), and Delta (DeltaG degrees ) are applied to help understand of the thermodynamic driving forces for retention and enantio-recognition for this chromatographic system. It can be concluded that the separations for all the investigated analytes on this CSP are enthalpically favored.
Chen
Xiaoping
X
School of Chemical Engineering & the Environment, Beijing Institute of Technology, Beijing100081, PR China.
Zhou
Zhiming
Z
Yuan
Hao
H
Meng
Zihui
Z