Gas chromatography—mass spectrometry of the stereoisomers of heterocyclic compounds. Part 1. Perhydrothioxanthenes

Adeeva, Valeriya G.; Bobyleva, M. S.; Kulikov, N. S.; Харченко, В. Г.; Yudovich, L. M.

doi:10.1039/p29920000965

Cited by 8 publications

(8 citation statements)

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“…25 For example, the conformational composition, separation on the GTC, and identification by chromatography coupled with mass spec trometry of stereoisomeric perhydrothioxanthenes, per hydroxanthenes, and perhydro 4 thia s indacenes have been studied earlier. 24,[33][34][35] Good agreement between the experimental and theoretically calculated TCA values (in particular, К 1,С and q -dif,1 ) for diverse stereoisomers was established 24,33-35 when the earlier 27,28 determined AAP parameters were used in the form of Eq. (2).…”

Section: Resultsmentioning

confidence: 99%

“…[18][19][20][21][22][23] This served as a reliable basis for the prediction of thermodynamic retention conditions on the GTC of many adamantane derivatives, a considerable part of which represented stereoisomers similar in proper ties. 20 The accumulated vast experimental material on the retention values on the GTC in combination with molecular statistical calculations was successfully used for the identification of particular isomers in complicated synthetic 24 and natural 25 mixtures.…”

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Molecular statistical calculation of thermodynamic characteristics of adsorption of O-, S-, and Se-containing heteroadamantanes on graphitized thermal carbon black

Yashkin

Svetlov²,

Murashov³

2010

Russ Chem Bull

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The thermodynamic characteristics of adsorption (TCA) on the basal face of graphite have been calculated in terms of the semiempirical molecular statistical theory of adsorption for molecules of O , S , and Se containing heteroadamantanes of different structure and isostructural cyclohexane derivatives. The influence of the nature, number, and position of heteroatoms in the adamantane framework on the TCA values was studied in detail, which made it possible to predict the retention of the compounds considered on the surface of graphitized thermal carbon black under the conditions of equilibrium gas adsorption chroma tography. The introduction of each subsequent heteroatom into a polyheteroadamantane molecule makes a non additive contribution to the TCA values. The contributions of various fragments to the total adsorption energy were calculated by the TCA of isostructural heterocyclohexane molecules, and the most preferential orientations of the framework molecules of the adsorbates relative to the planar graphite surface were determined.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Molecular statistical calculation of thermodynamic characteristics of adsorption of O-, S-, and Se-containing heteroadamantanes on graphitized thermal carbon black

Yashkin

Svetlov²,

Murashov³

2010

Russ Chem Bull

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“…This resembles the mass spectra of cis-cis, trans-cis and trans-trans isomers of PHTX. 1 Comparison of the stereospecific features of the fragmentation of PHTX and PHTI isomers might be useful for the structure elucidation of the latter.…”

Section: Resultsmentioning

confidence: 99%

“…Perhydro-4-thia-s-indacene (PHTI) theoretically exists as six diastereomers, as with its homologue perhydrothiaxanthene (PHTX) studied previously. 1 Like other tricyclic congeners, cis-syn-cis and cis-anti-cis isomers of PHTI can undergo inversion of the middle ring. The inversion proceeds through an intermediate conformation C with the middle ring as a boat.…”

Section: Introductionmentioning

confidence: 99%

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Gas chromatography–mass spectrometry of the stereoisomers of heterocyclic compounds. Part 3.† Perhydro-4-thia-s-indacene

Kulikov

Bobyleva

2000

J. Chem. Soc., Perkin Trans. 2

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A gas chromatographic-mass spectrometric study of mixtures of the stereoisomers of perhydro-4-thia-s-indacene (PHTI) has been carried out. Separation has been accomplished on a column packed with graphitized thermal carbon black (GTCB) and on a capillary column of high efficiency. In addition to the known cis-syn-cis isomer, five novel diastereomers have been found. The stereospecificity of their fragmentation under electron impact appeared to be quite distinct and mass spectra (70 eV) of cis-cis, trans-cis and trans-trans conjugated isomers were distinguished. An important part in the structural elucidation of the novel isomers is played by molecular statistical calculations of the thermodynamic parameters of their adsorption on GTCB, which were performed on the basis of hypothetical molecular structures of these compounds optimized by molecular mechanics. Evidence for the existence of cis-cis isomers with the middle ring in a boat conformation obtained from these data is discussed.

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Thiopyrans and their Benzo Derivatives

Hepworth

Heron

2008

Comprehensive Heterocyclic Chemistry III

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Gas chromatography—mass spectrometry of the stereoisomers of heterocyclic compounds. Part 1. Perhydrothioxanthenes

Abstract: Paper 1/06429K

Cited by 8 publications

References 12 publications

Molecular statistical calculation of thermodynamic characteristics of adsorption of O-, S-, and Se-containing heteroadamantanes on graphitized thermal carbon black

Molecular statistical calculation of thermodynamic characteristics of adsorption of O-, S-, and Se-containing heteroadamantanes on graphitized thermal carbon black

Gas chromatography–mass spectrometry of the stereoisomers of heterocyclic compounds. Part 3.† Perhydro-4-thia-s-indacene

Thiopyrans and their Benzo Derivatives

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