Studies on the mechanism of the peroxyoxalate chemiluminescence reaction: part 2. Further identification of intermediates using 2D EXSY 13C nuclear magnetic resonance spectroscopy

Analytica Chimica Acta
Sarah A TonkinNeil W Barnett

Abstract

Further consideration has been given to the reaction pathway of a model peroxyoxalate chemiluminescence system. Again utilising doubly labelled oxalyl chloride and anhydrous hydrogen peroxide, 2D EXSY (13)C nuclear magnetic resonance (NMR) spectroscopy experiments allowed for the characterisation of unknown products and key intermediate species on the dark side of the peroxyoxalate chemiluminescence reaction. Exchange spectroscopy afforded elucidation of a scheme comprised of two distinct mechanistic pathways, one of which contributes to chemiluminescence. (13)C NMR experiments carried out at varied reagent molar ratios demonstrated that excess amounts of hydrogen peroxide favoured formation of 1,2-dioxetanedione: the intermediate that, upon thermolysis, has been long thought to interact with a fluorophore to produce light.

References

Oct 31, 2002·Luminescence : the Journal of Biological and Chemical Luminescence·Sandra M SilvaWilhelm J Baader
Nov 22, 2002·Luminescence : the Journal of Biological and Chemical Luminescence·Sandra M SilvaWilhelm J Baader

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Citations

Apr 12, 2013·The Journal of Chemical Physics·Brett I DunlapAnguang Hu
Jan 18, 2017·The Journal of Physical Chemistry. a·Pooria Farahani, Wilhelm J Baader
Sep 29, 2019·Chemistry : a European Journal·Laura DelafresnayeChristopher Barner-Kowollik
Nov 17, 2019·Photochemistry and Photobiology·Maidileyvis C CabelloWilhelm J Baader
May 29, 2013·Photochemistry and Photobiology·Felipe A AugustoWilhelm J Baader
Oct 20, 2020·Photochemistry and Photobiology·Felipe A AugustoWilhelm J Baader
Feb 12, 2009·Journal of the American Chemical Society·Richard BosNeil W Barnett
Aug 29, 2009·The Journal of Organic Chemistry·Luiz F M L CiscatoWilhelm J Baader
Mar 2, 2018·Chemical Reviews·Morgane VacherRoland Lindh
Aug 24, 2021·The Journal of Organic Chemistry·Sandra M da SilvaWilhelm J Baader

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