Are the three hydroxyphenyl radical isomers created equal? - The role of the phenoxy radical -

P Hemberger; G da Silva; AJ Trevitt; T Gerber; A Bodi

Journal article

Are the three hydroxyphenyl radical isomers created equal? - The role of the phenoxy radical -

P Hemberger, G da Silva, AJ Trevitt, T Gerber, A Bodi

PHYSICAL CHEMISTRY CHEMICAL PHYSICS | ROYAL SOC CHEMISTRY | Published : 2015

DOI: 10.1039/c5cp05346c

Abstract

We have investigated the thermal decomposition of the three hydroxyphenyl radicals (˙C6H4OH) in a heated microtubular reactor. Intermediates and products were identified isomer-selectively applying photoion mass-selected threshold photoelectron spectroscopy with vacuum ultraviolet synchrotron radiation. Similarly to the phenoxy radical (C6H5-O˙), hydroxyphenyl decomposition yields cyclopentadienyl (c-C5H5) radicals in a decarbonylation reaction at elevated temperatures. This finding suggests that all hydroxyphenyl isomers first rearrange to form phenoxy species, which subsequently decarbonylate, a mechanism which we also investigate computationally. Meta- and para-radicals were selectively p..

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University of Melbourne Researchers

Gabriel da Silva Author Chemical Engineering

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Grants

Awarded by Swiss Federal Office for Energy

Awarded by Australian Research Council

Funding Acknowledgements

Experiments were carried out at the VUV beamline of the Swiss Light Source, Paul Scherrer Institute. The work was financially supported by the Swiss Federal Office for Energy (BFE Contract Numbers 101969/152433 & SI/501269-01). A. J. T. and G. d. S. acknowledge funding support from the Australian Research Council (DP130100862, DP110103889, and FT130101304). The authors want to thank Victoria Custodis for providing the phenoxy spectrum, Matthew B. Predergast for useful remarks and proofreading this manuscript, and Jana Hemberger for the table of contents drawing.