Characterization of tetra-aryl benzene isomers by using preparative gas chromatography with mass spectrometry, nuclear magnetic resonance spectroscopy, and x-ray crystallographic methods

Christian Ruhle, Julie Niere, Paul Morrison, Roderick Jones, Tom Caradoc-Davies, Allan Canty, Michael Gardiner, Vicki-Anne Tolhurst, Philip Marriott

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Abstract

The present study describes a preparative gas chromatographic (GC) approach employed to study a series of products arising from reaction of phenylacetylene with para-substituted aryl-iodides under Sonogashira catalysis conditions. GC analysis resolves the isomers from each reaction; however, it cannot provide structural details (their MS data are virtually identical). Since classical liquid chromatography cannot resolve the isomers, preparative-scale GC is the only practical approach to provide further spectroscopic characterization of the isomers. The products are well separated by GC so a single thick-film capillary column is adequate for this case, with operation up to similar to+300 degrees C. By collection of 50+ repeat injections, sufficient material could be isolated for H-1 NMR spectral analysis of the isomers, and for one isomer (isomer I) of a number of analogous related catalytic reaction mixtures, X-ray crystal structure determination enabled complete structural elucidation (absolute configuration) of the substitution pattern of the structure of this isomer. This confirmed isomer I to be the 2-para-aryl-substituted 1,3,5-triphenylbenzene product in all cases. 1H NMR spectra of isomer I products generally had similar patterns but differed markedly from the second major isomer product (isomer II).
Original languageEnglish
Pages (from-to)4501 - 4509
Number of pages9
JournalAnalytical Chemistry
Volume82
Issue number11
DOIs
Publication statusPublished - 2010
Externally publishedYes

Cite this

Ruhle, Christian ; Niere, Julie ; Morrison, Paul ; Jones, Roderick ; Caradoc-Davies, Tom ; Canty, Allan ; Gardiner, Michael ; Tolhurst, Vicki-Anne ; Marriott, Philip. / Characterization of tetra-aryl benzene isomers by using preparative gas chromatography with mass spectrometry, nuclear magnetic resonance spectroscopy, and x-ray crystallographic methods. In: Analytical Chemistry. 2010 ; Vol. 82, No. 11. pp. 4501 - 4509.
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title = "Characterization of tetra-aryl benzene isomers by using preparative gas chromatography with mass spectrometry, nuclear magnetic resonance spectroscopy, and x-ray crystallographic methods",
abstract = "The present study describes a preparative gas chromatographic (GC) approach employed to study a series of products arising from reaction of phenylacetylene with para-substituted aryl-iodides under Sonogashira catalysis conditions. GC analysis resolves the isomers from each reaction; however, it cannot provide structural details (their MS data are virtually identical). Since classical liquid chromatography cannot resolve the isomers, preparative-scale GC is the only practical approach to provide further spectroscopic characterization of the isomers. The products are well separated by GC so a single thick-film capillary column is adequate for this case, with operation up to similar to+300 degrees C. By collection of 50+ repeat injections, sufficient material could be isolated for H-1 NMR spectral analysis of the isomers, and for one isomer (isomer I) of a number of analogous related catalytic reaction mixtures, X-ray crystal structure determination enabled complete structural elucidation (absolute configuration) of the substitution pattern of the structure of this isomer. This confirmed isomer I to be the 2-para-aryl-substituted 1,3,5-triphenylbenzene product in all cases. 1H NMR spectra of isomer I products generally had similar patterns but differed markedly from the second major isomer product (isomer II).",
author = "Christian Ruhle and Julie Niere and Paul Morrison and Roderick Jones and Tom Caradoc-Davies and Allan Canty and Michael Gardiner and Vicki-Anne Tolhurst and Philip Marriott",
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Characterization of tetra-aryl benzene isomers by using preparative gas chromatography with mass spectrometry, nuclear magnetic resonance spectroscopy, and x-ray crystallographic methods. / Ruhle, Christian; Niere, Julie; Morrison, Paul; Jones, Roderick; Caradoc-Davies, Tom; Canty, Allan; Gardiner, Michael; Tolhurst, Vicki-Anne; Marriott, Philip.

In: Analytical Chemistry, Vol. 82, No. 11, 2010, p. 4501 - 4509.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Characterization of tetra-aryl benzene isomers by using preparative gas chromatography with mass spectrometry, nuclear magnetic resonance spectroscopy, and x-ray crystallographic methods

AU - Ruhle, Christian

AU - Niere, Julie

AU - Morrison, Paul

AU - Jones, Roderick

AU - Caradoc-Davies, Tom

AU - Canty, Allan

AU - Gardiner, Michael

AU - Tolhurst, Vicki-Anne

AU - Marriott, Philip

PY - 2010

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N2 - The present study describes a preparative gas chromatographic (GC) approach employed to study a series of products arising from reaction of phenylacetylene with para-substituted aryl-iodides under Sonogashira catalysis conditions. GC analysis resolves the isomers from each reaction; however, it cannot provide structural details (their MS data are virtually identical). Since classical liquid chromatography cannot resolve the isomers, preparative-scale GC is the only practical approach to provide further spectroscopic characterization of the isomers. The products are well separated by GC so a single thick-film capillary column is adequate for this case, with operation up to similar to+300 degrees C. By collection of 50+ repeat injections, sufficient material could be isolated for H-1 NMR spectral analysis of the isomers, and for one isomer (isomer I) of a number of analogous related catalytic reaction mixtures, X-ray crystal structure determination enabled complete structural elucidation (absolute configuration) of the substitution pattern of the structure of this isomer. This confirmed isomer I to be the 2-para-aryl-substituted 1,3,5-triphenylbenzene product in all cases. 1H NMR spectra of isomer I products generally had similar patterns but differed markedly from the second major isomer product (isomer II).

AB - The present study describes a preparative gas chromatographic (GC) approach employed to study a series of products arising from reaction of phenylacetylene with para-substituted aryl-iodides under Sonogashira catalysis conditions. GC analysis resolves the isomers from each reaction; however, it cannot provide structural details (their MS data are virtually identical). Since classical liquid chromatography cannot resolve the isomers, preparative-scale GC is the only practical approach to provide further spectroscopic characterization of the isomers. The products are well separated by GC so a single thick-film capillary column is adequate for this case, with operation up to similar to+300 degrees C. By collection of 50+ repeat injections, sufficient material could be isolated for H-1 NMR spectral analysis of the isomers, and for one isomer (isomer I) of a number of analogous related catalytic reaction mixtures, X-ray crystal structure determination enabled complete structural elucidation (absolute configuration) of the substitution pattern of the structure of this isomer. This confirmed isomer I to be the 2-para-aryl-substituted 1,3,5-triphenylbenzene product in all cases. 1H NMR spectra of isomer I products generally had similar patterns but differed markedly from the second major isomer product (isomer II).

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