Characterization of tetra-aryl benzene isomers by using preparative gas chromatography with mass spectrometry, nuclear magnetic resonance spectroscopy, and X-ray crystallographic methods
| Autor: | Allan J. Canty, Paul D. Morrison, Roderick C. Jones, Tom T. Caradoc-Davies, Christian P. G. Rühle, Philip J. Marriott, Michael G. Gardiner, Vicki-Anne Tolhurst, Julie O. Niere |
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| Rok vydání: | 2010 |
| Předmět: |
Magnetic Resonance Spectroscopy
Chemistry Acetylene Aryl Analytical chemistry Absolute configuration Sonogashira coupling Benzene Nuclear magnetic resonance spectroscopy Mass spectrometry Crystallography X-Ray Catalysis Gas Chromatography-Mass Spectrometry Analytical Chemistry chemistry.chemical_compound Phenylacetylene Isomerism Proton NMR Gas chromatography Iodine |
| Zdroj: | Analytical chemistry. 82(11) |
| ISSN: | 1520-6882 |
| Popis: | 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 approximately +300 degrees C. By collection of 50+ repeat injections, sufficient material could be isolated for (1)H 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. (1)H NMR spectra of isomer I products generally had similar patterns but differed markedly from the second major isomer product (isomer II). |
| Databáze: | OpenAIRE |
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