Gas chromatography-mass spectrometry of the stereoisomers of perhydroanthracene and perhydrophenanthrene

Киселев, А. В.; Kulikov, N. S.; Curthoys, Geoffrey

doi:10.1007/bf02259081

Cited by 9 publications

(9 citation statements)

References 12 publications

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“…7E) has a fragment ion M + -29 (m/z 191) of intensity equal to that of the molecular ion, suggesting the loss of an ethyl substituent from one of the terminal rings of the perhydroanthracene or perhydrophenantrene. Otherwise, the mass spectrum of peak E is similar to those published by Kiselev et al (1984). Detail of the fragmentation pattern is shown in figure 7E.…”

Section: Tricyclic Compoundssupporting

confidence: 70%

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Analysis of unresolved complex mixtures of hydrocarbons extracted from Late Archean sediments by comprehensive two-dimensional gas chromatography (GC×GC)

Ventura

Kenig

Reddy

et al. 2008

Organic Geochemistry

116

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Hydrocarbon mixtures too complex to resolve by traditional capillary gas chromatrography display gas chromatograms with dramatically rising baselines or "humps" of coeluting compounds that are termed unresolved complex mixtures (UCMs). Because the constituents of UCMs are not ordinarily identified, a large amount of geochemical information is never explored. Gas chromatograms of saturated/unsaturated hydrocarbons extracted from Late Archean argillites and greywackes of the southern Abitibi Province of Ontario, Canada contain UCMs with different appearances or "topologies" relating to the intensity and retention time of the compounds comprising the UCMs. These topologies appear to have some level of stratigraphic organization, such that samples collected at any stratigraphic formation collectively are dominated by UCMs that either elute early-(within a window of C 15 -C 20 of n-alkanes), earlyto mid-(C 15 -C 30 of n-alkanes), or have a broad UCM that extends through the entire retention time of the sample (from C 15 -C 42 of n-alkanes). Comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry (GC×GC-MS) was used to resolve the constituents forming these various UCMs. Early-to mid-eluting UCMs are dominated by configurational isomers of alkyl-substituted and non substituted polycyclic compounds that contain up to six rings. Late eluting UCMs are composed of C 36 -C 40 mono-, bi-, and tricyclic archaeal isoprenoid diastereomers. Broad UCMs spanning the retention time of compound elution contain nearly the same compounds observed in the early-, mid-, and late retention time UCMs. Although the origin of the polycyclic compounds is unclear, the variations in the UCM topology appear to depend on the concentration of initial compound classes that have the potential to become isomerized. Isomerization of these constituents may have resulted from hydrothermal alteration of organic matter.

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Section: Tricyclic Compoundssupporting

confidence: 70%

“…they do not have a fragment ion m/z 123). Interpretation of the mass spectrometric data was facilitated by Kiselev's et al (1984) study of perhydrophenanthrene and perhydroanthracene fragmentation. The mass spectrum of peak E (Fig.…”

Section: Tricyclic Compoundsmentioning

confidence: 99%

Analysis of unresolved complex mixtures of hydrocarbons extracted from Late Archean sediments by comprehensive two-dimensional gas chromatography (GC×GC)

Ventura

Kenig

Reddy

et al. 2008

Organic Geochemistry

116

View full text Add to dashboard Cite

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“…The elution order of PHX stereoisomers from the capillary column coated with the non-polar stationary liquid phase differs compared to the stereoisomers of PHA and PHTX. 1, 9 In particular, cis-syn-cis-PHX is the second species to appear on the chromatogram (X2, Fig. 1), whereas cis-syn-cis isomers of PHA and PHTX are the fifth isomers to elute.…”

Section: Resultsmentioning

confidence: 97%

“…The second condition is the most important and much In spite of its simplicity, a qualitative concept of location of stereoisomer molecules on the flat surface of GTCB has contributed to the structure elucidation of perhydroanthracenes (PHA), perhydrophenanthrenes (PHP) and perhydrothioxanthenes (PHTX) provided that their mass spectra appeared distinct. 1,9 This paper presents the results of a GC-MS study of the two mixtures of PHX stereoisomers having been synthesised according to the above-mentioned methods and kindly donated by Yudovich and co-workers and Blinokhvatov.…”

Section: Introductionmentioning

confidence: 99%

Gas chromatography–mass spectrometry of the stereoisomers of heterocyclic compounds. Part 2a.1 Perhydroxanthenes

Bobyleva¹,

Kulikov²

1998

J. Chem. Soc., Perkin Trans. 2

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“…A similar process was studied before as the stereo-specific feature of the fragmentation of PHA isomers. 10 [M Ϫ C 4 H 9 ] ϩ ions were predominantly formed from cis-syn-cis-PHA, which is involved in strong syn-axial intramolecular interactions. However, the formal comparison in this case is incorrect because for isomer cis-syn-cis (A) this process is not inherent.…”

Section: Resultsmentioning

confidence: 99%

Gas chromatography–mass spectrometry of the stereoisomers of heterocyclic compounds. Part 2b.1 Perhydroxanthenes

Kulikov¹,

Bobyleva²

1998

J. Chem. Soc., Perkin Trans. 2

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The quantitative relationships between the retention of the stereoisomers of perhydroxanthene (PHX) on a column packed with graphitized thermal carbon black (GTCB) and their hypothetical molecular structures optimized by molecular mechanics have been established. From the GC-MS data obtained the structure of four novel stereoisomers have been elucidated. Along with the theoretically expected trans-anti-trans-, trans-syn-cis-and cis-anti-cis-isomers, the unusual stable stereoisomeric form of PHX has been found and elucidated as conformer B of the cis-syn-cis-isomer. The evidence for this assignment based on the obtained GC-and MS-data is discussed.

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Gas chromatography-mass spectrometry of the stereoisomers of perhydroanthracene and perhydrophenanthrene

Cited by 9 publications

References 12 publications

Analysis of unresolved complex mixtures of hydrocarbons extracted from Late Archean sediments by comprehensive two-dimensional gas chromatography (GC×GC)

Analysis of unresolved complex mixtures of hydrocarbons extracted from Late Archean sediments by comprehensive two-dimensional gas chromatography (GC×GC)

Gas chromatography–mass spectrometry of the stereoisomers of heterocyclic compounds. Part 2a.1 Perhydroxanthenes

Gas chromatography–mass spectrometry of the stereoisomers of heterocyclic compounds. Part 2b.1 Perhydroxanthenes

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