Preparation and enantioseparation characteristics of a novel chiral stationary phase based on mono (6(A)-azido-6(A)-deoxy)-per(p-chlorophenylcarbamoylated) beta-cyclodextrin.
A novel cyclodextrin (CD) derivative-mono (6(A)-azido-6(A)-deoxy)-per(p-chlorophenylcarbamoylated) beta-CD was synthesized and chemically immobilized onto the surface of amino-functionalized silica gel to afford a structurally well-defined chiral stationary phase (CSP) for high performance liquid chromatography (HPLC). The p-chlorophenyl groups introduced on the beta-CD are pi-electron deficient (i.e., pi-acidic moieties); therefore the stronger pi-pi interaction which plays an important role in chiral recognition process is expected between aromatic analytes and this type of the CSP. The enantiomeric separations of 11 piperazine derivatives as well as six racemates have been successfully achieved on this CSP in the normal and reversed phase modes.
Zhang
Zhen-Bin
ZB
School of Chemistry & Environment, South China Normal University, GuangZhou 510006, China.
Zhang
Wei-Guang
WG
Luo
Wen-Jun
WJ
Fan
Jun
J
D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D009930:Organic Chemicals / Q000302:isolation & purification*; D058428:Silica Gel; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*
C535116:(6(A)-azido-6(A)-deoxy)-per(4-chlorophenylcarbamoylated)-beta-cyclodextrin; D001386:Azides; D009930:Organic Chemicals; D047392:beta-Cyclodextrins; D058428:Silica Gel; D012822:Silicon Dioxide