Substituent effects on chiral resolutions of derivatized 1‐phenylalkylamines by heptakis(2,3‐di‐O‐methyl‐6‐O‐tert‐butyldimethylsilyl)‐β‐cyclodextrin GC stationary phase

Abstract

Chiral resolutions of trifluoroacetyl-derivatized 1-phenylalkylamines with different type and position of substituent were investigated by capillary gas chromatography by using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin diluted in OV-1701 as a chiral stationary phase. The influence of column temperature on retention and enantioselectivity was examined. All enantiomers of meta-substituted analytes as well as fluoro-substituted analytes could be resolved. Temperature had a favorable influence on enantioselectivity for small amines with substituents at the ortho-position. The type of substituent at the stereogenic center of amines also had a crucial effect as the ethyl group led to poor enantioseparation. Among all analytes studied, trifluoroacetyl-derivatized 1-(2'-fluorophenyl)ethylamine exhibited baseline resolution with the shortest analysis time.

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

“…CD-containing chiral stationary phase (CSP) is extensively used in gas chromatography (GC), high-performance liquid chromatography (HPLC), thin-layer chromatography (TLC), micro solid phase extraction (μ-SPE), capillary electrophoresis (CE), capillary electrochromatography (CEC), electrokinetic chromatography (EKC), and supercritical fluid chromatography (SFC) for the separation of structurally similar compounds or complex product matrices of enantiomers [ 96 , 97 , 98 , 99 , 100 , 101 ]. The derivatization or coupling of CDs using various functional molecules is also widely employed in this field [ 102 , 103 , 104 , 105 , 106 , 107 , 108 , 109 , 110 , 111 , 112 ]. One such example can be seen in the study conducted by Sun et al, in which per-4-chlorophenylcarbamate/β-cyclodextrin-based CSP was developed and successfully applied for the separation of flurbiprofen enantiomers and 22 other drug racemates [ 109 , 110 ].…”

Click regulation of cyclodextrin primary face for the preparation of novel chiral stationary phases

“…Apart from the special structure, the hydroxyl groups on CD rims offer the possibility of modification. Owing to these superiorities, CDs are widely applied in various separation technologies , especially in HPLC . The development of CD‐chiral stationary phases (CSPs) mainly focuses on two terms: CD functionalization and spacer design .…”