Enantioseparation of Hydrobenzoin and Structurally Related Compounds on β-Cyclodextrin and Hydroxypropyl-β-cyclodextrin Bonded Chiral Stationary Phases

Yu, Guang‐Yan; Guo, Lizhen; Xie, Feiyun; Yao, Bixia; Zeng, Qingle; Weng, Wen

doi:10.1007/s10337-011-1995-5

Cited by 8 publications

(1 citation statement)

References 23 publications

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“…On the other hand, different retention models have been proposed to discuss the retention mechanism [35]; for example, the linear solvent strength (LSS) retention model expresses the relationship between the retention factor and the percentage of organic modifier in reversed-phase chromatography [35][36][37][38]. The stoichiometric displacement theory for retention (SDT-R) has also been proposed based on the assumption of five equilibria involving the solute, the bonded phase, and the organic solvent [39][40][41][42][43].…”

Section: Introductionmentioning

confidence: 99%

Reversal of Elution Order between Enantiomers of Binaphthol on an Immobilized Polysaccharide-Based Chiral Stationary Phase

et al. 2011

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Enantioseparation of 1,1 0 -bi-2-naphthol (BINOL) was performed on an immobilized polysaccharide-based chiral stationary phase (CSP), Chiralpak IA, in the normalphase mode. The effects of polar modifier in the mobile phase and column temperature on retention, enantioseparation, and elution order were investigated. An interesting reversal of elution order for BINOL was observed. When ethanol was used as a polar modifier, R-BINOL was eluted first with marginal enantioseparation. Excellent enantioseparation was obtained when ethanol was replaced by 1-propanol, and S-BINOL was eluted first, this effect being retained with 2-butanol, 1-butanol, 1-pentanol or 1-hexanol as the modifier. When isoamyl alcohol was used, reversal of elution order was again observed, i.e., R-BINOL eluted first with marginal enantioseparation, similar to the case of ethanol. When cyclohexanol and cyclopentanol were used, R-BINOL was still eluted first, but enantioseparation was as good as with 1-propanol as the modifier. This is the first report of large enantioseparation obtained in both elution orders for a given selector/selectant system. A retention model based on stoichiometric displacement theory for retention (SDT-R) was investigated to fit the chromatographic data. The reason for solvent-induced reversal of elution order was elucidated based on a derivation of the retention model. Reversal of elution order for BINOL induced by the content of isoamyl alcohol was also predicted based on the model and confirmed by experiment.

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Section: Introductionmentioning

confidence: 99%

Reversal of Elution Order between Enantiomers of Binaphthol on an Immobilized Polysaccharide-Based Chiral Stationary Phase

et al. 2011

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Enantioseparation of Flavanoids, Isoxazolines, Dansyl Amino Acids and β-Blockers on Native and Phenylcarbamoylated α, β and γ-Cyclodextrin Chiral Stationary Phases

2017

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In this study, a series of native and p‐methylphenylcarbamoylated cyclodextrin chiral stationary phases (CD‐CSPs) were developed based on α, β and γ‐cyclodextrin via ether linkage. The as‐prepared CSPs were characterized by FTIR, solid‐state C13 NMR, thermogravimetric analysis and elemental analysis. Their enantioseparation properties were comprehensively investigated by using high performance liquid chromatography (HPLC) with various racemates including flavanoids, isoxazolines, dansyl amino acids and β‐blockers. The effects of CD cavity size and CD functionalities on the enantioseparation results were evaluated in detail. The correlation between analyte structures and their chiral resolution were also investigated. A reference chart has been proposed for quick choice of CD‐CSPs for enantioseparation of specific racemates.

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Study on inclusion interaction of hydrophilic 2-chloromandelic acid with hydroxypropyl-β-cyclodextrin

Jiang

Zhou

et al. 2012

J Incl Phenom Macrocycl Chem

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Enantioseparation of Hydrobenzoin and Structurally Related Compounds on β-Cyclodextrin and Hydroxypropyl-β-cyclodextrin Bonded Chiral Stationary Phases

Cited by 8 publications

References 23 publications

Reversal of Elution Order between Enantiomers of Binaphthol on an Immobilized Polysaccharide-Based Chiral Stationary Phase

Reversal of Elution Order between Enantiomers of Binaphthol on an Immobilized Polysaccharide-Based Chiral Stationary Phase

Enantioseparation of Flavanoids, Isoxazolines, Dansyl Amino Acids and β-Blockers on Native and Phenylcarbamoylated α, β and γ-Cyclodextrin Chiral Stationary Phases

Study on inclusion interaction of hydrophilic 2-chloromandelic acid with hydroxypropyl-β-cyclodextrin

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