Enantiomeric separations of chiral polychlorinated biphenyls on three polysaccharide-type chiral stationary phases by supercritical fluid chromatography

Zhang, Anping; Gao, Weiliang; Ma, Binbin; Jin, Lixia; Lin, Chunmian

doi:10.1007/s00216-012-6063-y

Cited by 10 publications

(4 citation statements)

References 27 publications

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“…In this regard, chiral columns containing cellulose tris(4‐methylbenzoate) as chiral selectors furnished the best results. Lin and co‐workers reported the baseline enantioseparation of 17 chiral PCBs (Table ) using Sino‐Chiral OJ, Chiralcel OD, and Chiralpak IB (250 × 4.6 mm) as chiral columns by SCF . In this case, the preliminary screening was performed with a MP of 100% CO 2 at a FR of 2.0 mL/min and column temperature of 36°C.…”

Section: Liquid‐phase Enantioseparation Of Stable Atropisomersmentioning

confidence: 99%

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

et al. 2017

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The term Atropisomerism defines a type of enantiomerism that arises from hindered rotation around an axis that makes two rotational isomers enantiomers. Atropisomeric compounds are present in nature, being important building blocks of many biologically active compounds. Atropisomers have been extensively studied in environmental and toxicological chemistry and, in particular, separating them has become a need in specific fields as organic synthesis and pharmaceutical research. High-performance LC has been fruitfully applied in this context, and despite HPLC separation on chiral stationary phase is considered as mature technology nowadays, in the last years several advancements and applications contributed to study compounds where axial chirality is of utmost importance. Moreover, dynamic chromatography has been exploited as a versatile tool for kinetic studies of systems with slow internal motion gaining essential information on their stereodynamic behavior. On this basis, current topics and trends in liquid-phase chromatography enantioseparation of atropisomers are presented herein with specific focus on new representative applications with HPLC, covering years 2010-2016. Some examples concerning supercritical fluid chromatography applications are also reported. This review aims to provide the reader with a modern overview of the field to highlight the renewed interest toward the chemistry of molecules with atropisomeric properties. A systematic compilation of all published literature has not been attempted.

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Section: Liquid‐phase Enantioseparation Of Stable Atropisomersmentioning

confidence: 99%

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

et al. 2017

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“…Previous works demonstrated that an increase in column temperature often causes short retention and worse resolution . To investigate the effect of column temperature on the resolution of sulfoxaflor stereoisomers, it was increased from 10 to 30ºC with 5ºC increments in this study (Fig.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Determination of a Novel Chiral Insecticide, Sulfoxaflor, in Brown Rice, Cucumber and Apple by Normal‐Phase High‐Performance Liquid Chromatography

Chen

Dong

et al. 2014

Chirality

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An effective high-performance liquid chromatography method was developed for the stereoselective determination of a new sulfoximines insecticide, sulfoxaflor, in brown rice, cucumber and apple. Target compounds were extracted with acetonitrile and an aliquot cleaned with Cleanert PestiCarb/PSA (primary and secondary amine) cartridge. Five polysaccharide-based columns were investigated on the separation of sulfoxaflor stereoisomers and the best was achieved on a ChromegaChiral CCA column with n-hexane/ethanol/methanol (90:2:8, v/v/v) as mobile phase by UV detection at 220 nm at 20ºC. The resolutions of the four stereoisomers were 1.85, 1.54 and 3.08, and the elution order was identified by optical rotation and stereoisomers ratio. The mean recoveries of sulfoxaflor stereoisomers ranged from 77.1% to 99.3%, with relative standard deviations less than 8.9% at three concentration levels in all matrices. The limits of detection for all stereoisomers varied from 0.05 mg/kg to 0.07 mg/kg, while the limit of quantification did not exceed 0.22 mg/kg. The method was then successfully applied to determine the sulfoxaflor stereoisomers in authentic samples, confirming that it is convenient and reliable for stereoselective determination of sulfoxaflor stereoisomers in food.

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“…Lin and colleagues reported the baseline enantioseparation of 17 out of 18 chiral PCBs (Table 13) using Sino-Chiral OJ, Chiralcel OD, and Chiralpak IB (250 × 4.6 mm) as chiral columns by SCF. 64 In this case, the preliminary screening was performed with a mobile phase of 100% CO 2 at a flow rate of 2.0 ml/min at a column temperature of 36°C. As reported in Table 14, some separations were optimized by adding alcoholic modifiers to the mobile phase.…”

Section: Polychlorinated Biphenyls and Derivativesmentioning

confidence: 99%

Liquid Chromatography Enantioseparations of Halogenated Compounds on Polysaccharide‐Based Chiral Stationary Phases: Role of Halogen Substituents in Molecular Recognition

2015

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Halogenated chiral molecules have become important in several fields of science, industry, and society as drugs, natural compounds, agrochemicals, environmental pollutants, synthetic products, and chiral supports. Meanwhile, the perception of the halogen moiety in organic compounds and its role in recognition processes changed. Indeed, the recognition of the halogen bond as an intermolecular interaction occurring when the halogen acts as a Lewis acid had a strong impact, particularly in crystal engineering and medicinal chemistry. Due to this renewed interest in the potentialities of chiral organohalogens, here we focus on selected recent applications dealing with enantioseparations of halogenated compounds on polysaccharide-based chiral stationary phases (CSPs), widely used in liquid chromatography (LC). In particular, recently the first case of halogen bonding-driven high-performance LC (HPLC) enantioseparation was reported on a cellulose-based CSP. Along with enantioseparations performed under conventional HPLC, representative applications using supercritical fluid chromatography (SFC) are reported.

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Enantiomeric separations of chiral polychlorinated biphenyls on three polysaccharide-type chiral stationary phases by supercritical fluid chromatography

Cited by 10 publications

References 27 publications

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

Stereoselective Determination of a Novel Chiral Insecticide, Sulfoxaflor, in Brown Rice, Cucumber and Apple by Normal‐Phase High‐Performance Liquid Chromatography

Liquid Chromatography Enantioseparations of Halogenated Compounds on Polysaccharide‐Based Chiral Stationary Phases: Role of Halogen Substituents in Molecular Recognition

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