Formation and stability of gas-phase o-benzoquinone from oxidation of ortho-hydroxyphenyl: A combined neutral and distonic radical study

Prendergast, Matthew B.; Kirk, Benjamin B.; Savee, John D.; Osborn, David L.; Taatjes, Craig A.; Masters, Kye -Simeon; Blanksby, Stephen J.; da Silva, Gabriel; Trevitt, Adam J.

doi:10.1039/C5CP02953H

Formation and stability of gas-phase o-benzoquinone from oxidation of ortho-hydroxyphenyl: A combined neutral and distonic radical study

Journal Article · Mon Oct 19 00:00:00 EDT 2015 · Physical Chemistry Chemical Physics. PCCP

DOI:https://doi.org/10.1039/C5CP02953H· OSTI ID:1329619

Prendergast, Matthew B. ^[1]; Kirk, Benjamin B. ^[2]; Savee, John D. ^[3]; Osborn, David L. ^[3]; Taatjes, Craig A. ^[3]; Masters, Kye -Simeon ^[4]; Blanksby, Stephen J. ^[4]; da Silva, Gabriel ^[5]; Trevitt, Adam J. ^[1]

Univ. of Wollongong, Wollongong (Australia)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Queensland Univ. of Technology, Brisbane (Australia)
The Univ. of Melbourne, Melbourne (Australia)

Gas-phase product detection studies of o-hydroxyphenyl radical and O₂ are reported at 373, 500, and 600 K, at 4 Torr (533.3 Pa), using VUV time-resolved synchrotron photoionisation mass spectrometry. The dominant products are assigned as o-benzoquinone (C₆H₄O₂, m/z 108) and cyclopentadienone (C₅H₄O, m/z 80). It is concluded that cyclopentadienone forms as a secondary product from prompt decomposition of o-benzoquinone (and dissociative ionization of o-benzoquinone may contribute to the m/z 80 signal at photon energies ≳9.8 eV). Ion-trap reactions of the distonic o-hydroxyphenyl analogue, the 5-ammonium-2-hydroxyphenyl radical cation, with O₂ are also reported and concur with the assignment of o-benzoquinone as the dominant product. In addition, the ion-trap study also provides support for a mechanism where cyclopentadienone is produced by decarbonylation of o-benzoquinone. Kinetic studies compare oxidation of the ammonium-tagged o-hydroxyphenyl and o-methylphenyl radical cations along with trimethylammonium-tagged analogues. Reaction efficiencies are found to be ca. 5% for both charge-tagged o-hydroxyphenyl and o-methylphenyl radicals irrespective of the charged substituent. G3X-K quantum chemical calculations are deployed to rationalise experimental results for o-hydroxyphenyl + O₂ and its charge-tagged counterpart. The prevailing reaction mechanism, after O₂ addition, involves a facile 1,5-H shift in the peroxyl radical and subsequent elimination of OH to yield o-benzoquinone that is reminiscent of the Waddington mechanism for β-hydroxyperoxyl radicals. These results suggest o-hydroxyphenyl + O₂ and decarbonylation of o-benzoquinone serve as plausible OH and CO sources in combustion.

View Accepted Manuscript (DOE)

Research Organization:: Sandia National Laboratories (SNL-CA), Livermore, CA (United States)

Sponsoring Organization:: USDOE Advanced Research Projects Agency - Energy (ARPA-E)

Grant/Contract Number:: AC04-94AL85000

OSTI ID:: 1329619

Alternate ID(s):: OSTI ID: 1439984

Report Number(s):: SAND--2016-10073J; 648109

Journal Information:: Physical Chemistry Chemical Physics. PCCP, Journal Name: Physical Chemistry Chemical Physics. PCCP Journal Issue: 6 Vol. 18; ISSN 1463-9076; ISSN PPCPFQ

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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