Separation of α- and β-pinene into enantiomers in gas-liquid chromatography systems via α-cyclodextrin inclusion complexes

Kościelski, Tomasz; Sybilska, Danuta; Jurczak, Janusz

doi:10.1016/s0021-9673(00)91547-4

Cited by 141 publications

(44 citation statements)

References 5 publications

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“…78 It is of interest to note that early trials in enantioselective GC witnessed the use of packed columns containing a hydrogen-bondingtype CSP (a dipeptide), 2 a coordination-type CSP (2 in squalane), 79 and an inclusion-type CSP (native a-cyclodextrin hydrate in formamide). 80 The invertomers of the chiral nitrogen pyramidyl compound 1-chloro-2,2-dimethylaziridine have been separated by preparative enantioselective complexation o-GC on 4a in squalane and the high enantiomeric excess ee of the isolated enantiomers was established via analytical complexation GC. 51 The amount of the isolated invertomers (approximately 2 mg each) was sufficient for the determination of chiroptical data.…”

Section: (Semi)preparative-scale Separation Of Enantiomers By Gcmentioning

confidence: 99%

Contributions to the theory and practice of the chromatographic separation of enantiomers

Schurig

2005

Chirality

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The theory and practice of enantioselective capillary chromatography employing metal coordination compounds and modified cyclodextrins as chiral stationary phases are treated. A unified approach involving all contemporary chromatographic methods and a single enantioselective column is described. Reliable thermodynamic data of enantioselectivity are derived by the retention-increment method. The existence of an isoenantioselective temperature is demonstrated. Kinetic enantiomerization studies are presented. The preparative-scale separation of enantiomers by gas chromatography with enantioselective packed columns is achieved. Unusual phenomena and future aspects of enantioselective chromatography are discussed.

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Section: (Semi)preparative-scale Separation Of Enantiomers By Gcmentioning

confidence: 99%

Contributions to the theory and practice of the chromatographic separation of enantiomers

Schurig

2005

Chirality

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“…In a two-necked roundbottomed flask (100 ml) equipped with magnetic stirrer and nitrogen inlet were added 6-O-TBDMS-b-CD (3 g, 1.55 mmol) previously dried under vacuum, anhydrous THF (60 ml), and 65 mg of NaH (1.63 mmol, oil dispersion 60%). The suspension was stirred for 12 h at 22jC and then heated under reflux for 1 h. After the suspension had cooled at 20jC, 324 mg of p-toluenesulfonyl chloride (1.7 mmol) was added and stirred for 90 min; TLC analysis, CHCl 3 /MeOH 8:2, R f = 0.6; work-up: the product was extracted with EtOAc, washed with brine, and dried over anhydrous Na 2 34 …”

Section: General Methodsmentioning

confidence: 99%

“…1 They have been successfully used to discriminate between functional groups, homologues, positional isomers and enantiomers. Since the early 1980s, 2 CD derivatives, mostly diluted with polysiloxanes, 3 have strongly contributed to the success of enantioselective gas chromatography (ES-GC), 4 -6 and a large number of alkylated, acylated, and partially silylated CDs have been synthesized and used as efficient chiral selectors in ES-GC. As other chemical and physical properties, CD enantioselectivity depends on ring size and on nature, number, and location of substituents in positions 2, 3, and 6.…”

mentioning

confidence: 99%

New chiral selectors: Design and synthesis of 6‐TBDMS‐2,3‐methyl β‐cyclodextrin 2‐2′ thioureido dimer and 6‐TBDMS‐2,3‐methyl (or 2‐methyl‐3‐acetyl) β‐cyclodextrin bearing an (R) mosher acid moiety

et al. 2004

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Cyclodextrin (CD) derivatives are important selectors for analytical chiral recognition. Their enantioselectivities and chemical properties depend on ring size and on nature, number and location of substituents. This paper describes the synthesis of 6-O-TBDMS-2,3-O-methyl beta-cyclodextrins bearing in position 2 either a single (R)-Mosher acid moiety or a second CD unit, in view of their possible application as chiral selectors. Most synthetic steps were successfully carried out under high-intensity ultrasound using a new sonochemical reactor developed in the authors' laboratory. 6-O-TBDMS-2-O-methyl-3-[(S)-2-methylbutyl]-beta-CD was also synthesized and tested with gas chromatography; the enantiorecognition power of the other CD derivatives is also being tested. A computational study of model structures to design these CD derivatives.

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“…6). A breakthrough was achieved by Kościel-ski et al who gas chromatographically enantioseparated the cycloalkenes a-and b-pinene 7 and the cycloalkanes trans-and cis-pinane 8 on packed columns containing Celite coated with a-cyclodextrin in formamide. The large enantioseparation factors a observed truly compensated the low efficiency of the set-up toward reasonable resolutions.…”

Section: Introductionmentioning

confidence: 99%

Gas chromatographic enantioseparation of unfunctionalized chiral alkanes: A challenge in separation science (overview, state of the art, and perspectives)

et al. 2008

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The chromatographic enantioseparation of small unfunctionalized chiral alkanes C*HR(1)R(2)R(3) (R = alkyl) represents a challenge in separation science. Because of the lack of any functional groups, enantiorecognition in the presence of a chiral selector is solely based upon weak enantioselective Van der Waals forces. Racemic alkanes containing seven and eight carbon atoms, i.e. 3-methylhexane (C7), 2,3-dimethylpentane (C7), 3-methylheptane (C8), 3,4-dimethylhexane (C8), 2,4-dimethylhexane (C8), 2,3-dimethylhexane (C8), and 2,2,3-trimethylpentane (C8) have been gas chromatographically enantioseparated on different modified cyclodextrins. The substitution pattern and cavity size of the cyclodextrin selectors have a pronounced effect on the degree of enantiorecognition observed. Thermodynamic parameters of enantiorecognition between four chiral alkanes and octakis(6-O-methyl-2,3-di-O-pentyl)-gamma-cyclodextrin (Lipodex G) have been determined. The possible role of molecular inclusion is indicated by the complete loss of enantioselectivity when the cyclodextrins are replaced by the corresponding linear dextrins ("acyclodextrins"). The enantioseparations of all seven chiral C7-C8 alkanes, six of them simultaneously, has been achieved on mixed binary selector systems whereby two different modified cyclodextrins are present in one gas chromatographic column. The smallest chiral (nonisotopically labeled) allene, i.e., 2,3-pentadiene, has been resolved gas chromatographically on a cyclodextrin selector.

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Separation of α- and β-pinene into enantiomers in gas-liquid chromatography systems via α-cyclodextrin inclusion complexes

Cited by 141 publications

References 5 publications

Contributions to the theory and practice of the chromatographic separation of enantiomers

Contributions to the theory and practice of the chromatographic separation of enantiomers

New chiral selectors: Design and synthesis of 6‐TBDMS‐2,3‐methyl β‐cyclodextrin 2‐2′ thioureido dimer and 6‐TBDMS‐2,3‐methyl (or 2‐methyl‐3‐acetyl) β‐cyclodextrin bearing an (R) mosher acid moiety

Gas chromatographic enantioseparation of unfunctionalized chiral alkanes: A challenge in separation science (overview, state of the art, and perspectives)

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