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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

Citation

Ruehle, CPG and Niere, J and Morrison, PD and Jones, RC and Caradoc-Davies, T and Canty, AJ and Gardiner, MG and Tolhurst, V and Marriott, PJ, Characterization of tetra-aryl benzene isomers by using preparative gas chromatography with mass spectrometry, nuclear magnetic resonance spectroscopy, and x-ray crystallographic methods, Analytical Chemistry, 82, (11) pp. 4501-4509. ISSN 0003-2700 (2010) [Refereed Article]

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Copyright Statement

Copyright 2010 American Chemical Society

Official URL: http://pubs.acs.org/journal/ancham

DOI: doi:10.1021/ac100417h

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 +300 C. By collection of 50+ repeat injections, sufficient material could be isolated for 1H 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).

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Inorganic Chemistry
Research Field:Transition Metal Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Jones, RC (Dr Roderick Jones)
Author:Canty, AJ (Professor Allan Canty)
Author:Gardiner, MG (Associate Professor Michael Gardiner)
Author:Tolhurst, V (Dr Vicki-Anne Gardiner)
ID Code:64665
Year Published:2010
Web of Science® Times Cited:14
Deposited By:Chemistry
Deposited On:2010-08-16
Last Modified:2011-05-11
Downloads:1 View Download Statistics

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