Enantiomer Separation of Cycloalkanols by Capillary Gas Chromatography on Cyclodextrin Phases
3
Citation
0
Reference
10
Related Paper
Abstract:
The enantiomers of 14 mono-, di-, tri-, and tetramethyl cyclohexanols, 2-methylcycloheptanol, and 2-methylcyclooctanol are separated with capillary gas-liquid chromatography on permethylated α- and β-cyclodextrin, respectively, dissolved in the polysiloxane phase OV-1701. Thermodynamic data are determined in order to investigate the mode of interaction of the enantiomers with the two chiral stationary phases. Besides this, there is no apparent relationship between the differences in retention indices on chiral and achiral stationary phases and the thermodynamic data of interaction with the chiral selector.Keywords:
Capillary gas chromatography
Cyclohexanol
Abstract Four chiral stationary phases were prepared by the immobilization of arylcarbamoylated β‐cyclodextrin onto functionalized silica gel via a long covalent linkage. Silica gel was glycidoxy‐functionalized, followed by amino‐functionalization with 1,6‐diaminohexane for further reaction to yield a long chain spacer. The structures of all compounds prepared were characterized by FT‐IR, 1H NMR, 13C NMR, and elemental analysis. From the data of elemental analysis, the surface concentrations of the spacer and the derivatized β‐cyclodextrin on silica gel were determined, and the results showed that on average, of eight spacers on silica gel, only one was linked to β‐cyclodextrin derivative. The enantioseparation capability of the four prepared chiral columns was evaluated by high performance liquid chromatography. The chiral stationary phase that was prepared from phenylcarbamoylated β‐cyclodextrin showed the best enantioseparation capability towards a wide variety of racemic mixtures. The chiral stationary phase that was prepared from 3,5‐dimethylphenylcarbmoylated β‐cyclodextrin showed good enantioseparation capability for pyrimidine derivatives. The chiral stationary phases that were prepared, respectively, from 1‐naphthylcarbamoylated β‐cyclodextrin and 2‐methoxyphenylcarbamoylated β‐cyclodextrin were less effective for enantioseparation.
Proton NMR
Cite
Citations (9)
A review of beta-cyclodextrin bonded stationary phases in chiral liquid chromatography is given, focusing on design and synthesis of beta-cyclodextrin bonded chiral stationary phases. Fifty-three references are presented in this paper.
BETA (programming language)
Chiral stationary phase
Beta-Cyclodextrins
Cite
Citations (0)
Abstract Both β-cyclodextrin and 2,3-methylated-β-cyclodextrin bonded stationary phases effectively separate a variety of structural and geometrical isomeric compounds in the reversed phase mode. The retention of neutral structural isomeric compounds, as well as substituted phenols and anilines, was usually longer on the methylated cyclodextrin stationary phase. Conversely, the retention of all substituted carboxylic acids was greater on the native β-cyclodextrin stationary phase. The selectivity differences between the native β-cyclodextrin and its 2,3-methylated analogue were not as great as expected for the structural isomers. In general, the structural isomer that was retained longest on the native β-cyclodextrin stationary phase also was retained longest on the 2,3-methylated cyclodextrin stationary phase. Current address: Advanced Separation Technologies, Inc., Whippany, NJ. Notes Current address: Advanced Separation Technologies, Inc., Whippany, NJ.
Structural isomer
Cite
Citations (14)
Abstract The use of α-, β-, and γ-cyclodextrin bonded stationary phases as multimodal support in HPLC is discussed. These supports are being used as reversedphase and normal phase for the separation of widely different groups of compounds. Also, they are used as for the separation of optical, geometrical, positional and structural isomers in addition to ions and organo-metallic compounds. A brief discussion of separation mechanisms and application and their use with other stationary phases to improve selectivity are also presented.
Structural isomer
Cite
Citations (15)
Capillary gas chromatography
Cite
Citations (4)
Chromatographic Separation
Cite
Citations (27)
A 2,6-di-O-propyl-β-cyclodextrin bonded stationary phase(PCDS) was prepared. The resulted bonded silica was characterized by three methods. The chromatographic performances of PCDS by separating isomers were investigated, and its retention mechanism was also discussed.
Cite
Citations (0)
摘要:
Cite
Citations (2)
Benzene derivatives
Cite
Citations (33)
A 4,4-dihydroxydiphenyl-bridged β-cyclodextrin bonded stationary phase(β-CD-D2-CSP) was prepared. The resulting bonded silica has been characterized by various methods. The chromatographic performances of β-CD-D2-CSP used for isomers' separation were investigated, and their mechanism of retention was discussed.
Characterization
Cite
Citations (0)