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1,2-Dioxetanedione

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1,2-Dioxetanedione
Names
IUPAC name
1,2-Dioxetane-3,4-dione
Other names
Peroxyacid ester
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1/C2O4/c3-1-2(4)6-5-1
    Key: WYNZXNXFHYJUTE-UHFFFAOYAI
  • O=C1OOC1=O
Properties
C2O4
Molar mass 88.018 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1] It quickly decomposes to carbon dioxide (CO2) even at 180 K (−93 °C)*, but can be detected by mass spectrometry and other techniques.[2][3] It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.

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

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: 9780471056249 ISBN: 9780470187203 John Wiley & Sons.
  2. ^ Herman F. Cordes, Herbert P. Richter, Carl A. Heller (1969). "Mass spectrometric evidence for the existence of 1,2-dioxetanedione (carbon dioxide dimer). Chemiluminescent intermediate". J. Am. Chem. Soc. 91 (25): 7209. doi:10.1021/ja01053a065.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ J. Stauff, W. Jaeschke, G. Schlögl (1972). Z. Naturforsch. B 27: 1434. {{cite journal}}: Missing or empty |title= (help)CS1 maint: multiple names: authors list (link)
  4. ^ Richard Bos, Neil W. Barnett, Gail A. Dyson, Kieran F. Lim, Richard A. Russell and Simon P. Watson (2003). "Studies on the mechanism of the peroxyoxalate chemiluminescence reaction: Part 1. Confirmation of 1,2-dioxetanedione as an intermediate using 13C nuclear magnetic resonance spectroscopy". Analytica Chimica Acta. 502 (2): 141–147. doi:10.1016/j.aca.2003.10.014.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ Richard Bos, Sarah A. Tonkin, Graeme R. Hanson, Christopher M. Hindson, Kieran F. Lim, and Neil W. Barnett (2009). "In Search of a Chemiluminescence 1,4-Dioxy Biradical". J. Am. Chem. Soc. 131 (8): 2770–2771. doi:10.1021/ja808401p.{{cite journal}}: CS1 maint: multiple names: authors list (link)


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