Development of gas chromatographic methods for determining the enantiomeric composition of organic compounds

Stan'kov, I. N.; Tarasov, S. N.; Agureyev, V.G.; Beresnev, A. N.; Lysenko, V.; Lanin, S. N.

doi:10.1016/0003-2670(91)87140-3

Cited by 4 publications

(12 citation statements)

References 12 publications

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“…(8) to the quantitative determination of enantiomeric composition was supported previously with symmetrical diastereomers prepared from the alkyl esters of amino esters with D and L configurations at different ratios between the components and a bifunctional achiral agent (phosgene) [7]. In this work, we demonstrated that this formula can also be…”

Section: Derivation Of An Equation For Calculating the Enantiomeric Cmentioning

confidence: 84%

“…Several reagents meet these requirements; among them are phosgene, carbon disulfide, phosphorus acid dichlorides, sulfuryl chloride, bromochloromethane, the DMSO-trimethylchlorosilane system, dimethylchlorosilane, and dibromoethane. Phosgene was successfully used for determining the enantiomeric composition of amino acids [7,8]. In this work, we used racemic 2-octanol and its optically pure D and L isomers as model substances.…”

Section: Resultsmentioning

confidence: 99%

“…The difference in the free energies of the interaction (∆(∆G)) of diastereomers with a stationary liquid phase is several tens of J/mol, whereas the free energy of the interaction is estimated at several thousands of J/mol [8,12]; therefore, the separation of diastereomers is a complicated problem.…”

Section: Choice Of Separation Conditions For Symmetrical Diastereomersmentioning

confidence: 99%

“…Previously [7], a statistical probability approach was used for the mathematical description of the composition of the resulting four-component mixture. In terms of the probability theory for a binary mixture of components Ä 1 and Ä 2 (see scheme (1)), the amounts of these components are expressed as A (wt %) and (100 -A) (wt %), respectively, or by equivalent probability numbers (p and (1 -p)).…”

Section: Derivation Of An Equation For Calculating the Enantiomeric Cmentioning

confidence: 99%

“…This technique was tested in determining the enantiomeric composition of various α -amino acid esters with the use of carbonic acid dichloride and carbon disulfide as bifunctional achiral reagents [6,7].…”

mentioning

confidence: 99%

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Gas-chromatographic determination of the enantiomeric composition of optically active alcohols and amines using achiral bifunctional reagents

et al. 2005

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A technique for determining the enantiomeric composition of 2-octanol and α -phenylethylamine with the use of gas chromatography on optically inactive stationary phases is proposed. The technique is based on the formation of symmetrical 1 diastereomeric derivatives upon the interaction of enantiomers with bifunctional achiral reagents: dimethyldichlorosilane, bromochloromethane, and dibromoethane. The reagents were chosen from the viewpoint of the synthesis of diastereomers with a minimum distance between the chiral centers. This minimum distance is responsible for a difference in the energies of interaction of the derivatives with the stationary liquid phase, which is sufficient for the separation of these derivatives.

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Section: Derivation Of An Equation For Calculating the Enantiomeric Cmentioning

confidence: 84%

Section: Resultsmentioning

confidence: 99%

Section: Choice Of Separation Conditions For Symmetrical Diastereomersmentioning

confidence: 99%

Section: Derivation Of An Equation For Calculating the Enantiomeric Cmentioning

confidence: 99%

mentioning

confidence: 99%

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Gas-chromatographic determination of the enantiomeric composition of optically active alcohols and amines using achiral bifunctional reagents

et al. 2005

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Gas-Chromatographic Separate Determination of Trace β-Chlorovinylarsonous Dichloroanhydride (Lewisite) and Anhydride (Lewisite Oxide) in Soil and Construction Materials

et al. 2005

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A method was proposed for the separate gas-chromatographic determination of β -chlorovinylarsonous dichloroanhydride (lewisite) and anhydride (lewisite oxide) in samples of soil and construction materials. Because of the absence of regulations for the maximum permissible concentration (MPC) of lewisite and lewisite oxide in construction materials (concrete, bricks, facing tile, etc.), the MPC level of lewisite in soil (0.1 mg/kg) was taken as the maximum permissible concentration in the development of the method for their determination in the above samples. The method is based on the solid-liquid extraction converting lewisite and lewisite oxide into components that can be separated at the stage of blowing-out the extractant in an inert gas flow and their subsequent conversion into acetylene with a 30% aqueous solution of sodium hydroxide and the chromatography of the vapor phase with flame-ionization detection. The error in the determination is no larger than ± 20 rel %. The time of analysis is within 1.5 h.

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Enantiomeric analysis of chiral compounds using phosphorus acid chlorides

et al. 2013

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New achiral separating bifunctional reagents, dichlorides of methylphosphonic and O ethyl thio phophoric acids, have been used for the quantitative determination of the enantiomeric composition of α amino acids (alanine, valine, proline), secondary alcohols (2 octanol, 2 pentanol, 1 methoxy 2 pro panol) and α phenylethylamine. The determination of the enantiomeric composition of optically active α amino acids, secondary alcohols, and amines is based on the transformation of compounds into symmetric diastereometers using organophosphorous achiral bifunctional reagents followed by the determination of the derivatives by gas chromatography with a mass spectral detector.

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Development of gas chromatographic methods for determining the enantiomeric composition of organic compounds

Cited by 4 publications

References 12 publications

Gas-chromatographic determination of the enantiomeric composition of optically active alcohols and amines using achiral bifunctional reagents

Gas-chromatographic determination of the enantiomeric composition of optically active alcohols and amines using achiral bifunctional reagents

Gas-Chromatographic Separate Determination of Trace β-Chlorovinylarsonous Dichloroanhydride (Lewisite) and Anhydride (Lewisite Oxide) in Soil and Construction Materials

Enantiomeric analysis of chiral compounds using phosphorus acid chlorides

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