1,2-Dioxetanedione

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1,2-Dioxetanedione
1,2-Dioxetanedione.svg
Names
IUPAC name
1,2-Dioxetane-3,4-dione
Other names
Peroxyacid ester
Identifiers
26974-08-3 N
ChemSpider 11535432 YesY
Jmol 3D model Interactive image
PubChem 14833747
  • InChI=1S/C2O4/c3-1-2(4)6-5-1 YesY
    Key: WYNZXNXFHYJUTE-UHFFFAOYSA-N YesY
  • InChI=1/C2O4/c3-1-2(4)6-5-1
    Key: WYNZXNXFHYJUTE-UHFFFAOYAI
  • O=C1OOC1=O
Properties
C2O4
Molar mass 88.02 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

The chemical compound 1,2-dioxetanedione, or 1,2-dioxacyclobutane-3,4-dione, often called peroxyacid ester, is an unstable oxide of carbon (an oxocarbon) with formula C2O4. It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.[1]

In ordinary conditions, it quickly decomposes to carbon dioxide (CO2) even at Lua error in Module:Convert at line 272: attempt to index local 'cat' (a nil value)., but can be detected by mass spectrometry and other techniques.[2][3]

1,2-Dioxetanedione is an intermediate in the chemoluminescent reactions used in glowsticks.[4] The decomposition proceeds via a paramagnetic oxalate biradical intermediate.[5]

Recently it has been found that a high-energy intermediate in one of these reactions (between oxalyl chloride and hydrogen peroxide in ethyl acetate), which is presumed to be 1,2-dioxetanedione, can accumulate in solution at room temperature (up to a few micromoles at least), provided that the activating dye and all traces of metals and other reducing agents are removed from the system, and the reactions are carried out in an inert atmosphere.[6]

See also

References

  1. Alfred Hassner (1985): Chemistry of Heterocyclic Compounds: Small Ring Heterocycles, Part 3: Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others, Volume 42. ISBN 978-0-471-05624-9 ISBN 978-0-470-18720-3 John Wiley & Sons.
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  6. Luiz F. M. L. Ciscato, Fernando H. Bartoloni, Erick L. Bastos, and Wilhelm J. Baader (2009), Direct Kinetic Observation of the Chemiexcitation Step in Peroxyoxalate Chemiluminescence. Journal of Organic Chemistry, volume 74, 8974–8979. doi:10.1021/jo901402k.