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Oxalic anhydride

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Oxalic anhydride
Names
Preferred IUPAC name Oxiranedione
Other names oxalic anhydride
ethanedioic anhydride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2O3/c3-1-2(4)5-1Key: PFPYHYZFFJJQFD-UHFFFAOYSA-N
  • InChI=1/C2O3/c3-1-2(4)5-1Key: PFPYHYZFFJJQFD-UHFFFAOYAE
SMILES
  • O=C1OC1=O
Properties
Chemical formula C2O3
Molar mass 72.019 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Oxalic anhydride or ethanedioic anhydride, also called oxiranedione, is a hypothetical organic compound, one of several isomers having the formula C2O3 that have been studied computationally. It can be viewed as the anhydride of oxalic acid or the two-fold ketone of ethylene oxide. It is an oxide of carbon (an oxocarbon).

The simple compound apparently has yet to be observed (as of 2009). In 1998, however, Paolo Strazzolini and others have claimed the synthesis of dioxane tetraketone (C4O6), which can be viewed as the cyclic dimer of oxalic anhydride.

It has been conjectured to be a fleeting intermediate in the thermal decomposition of certain oxalates and certain chemoluminescent reactions of oxalyl chloride.

See also

References

  1. Paolo Strazzolini; Alberto Gambi; Angelo G. Giumanini; Hrvoj Vancik (1998). "The reaction between ethanedioyl (oxalyl) dihalides and Ag2C2O4: a route to Staudinger's elusive ethanedioic (oxalic) acid anhydride". J. Chem. Soc., Perkin Trans. 1 (16): 2553–2558. doi:10.1039/a803430c.
  2. Ahmed A. El-Sherif; Bakir J. A. Jeragh (2007). "Mixed ligand complexes of Cu(II)-2-(2-pyridyl)-benzimidazole and aliphatic or aromatic dicarboxylic acids: Synthesis, characterization and biological activity". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 68 (1): 877–882. Bibcode:2007AcSpA..68..877E. doi:10.1016/j.saa.2006.12.073. PMID 17320475.
  3. M. M. Rauhut; L. J. Bollyky; R. A. Clarke; M. Loy; B. G.Roberts (September 30, 1965). Chemiluminescent Materials (AD0621845) (PDF) (Technical report). Office of Naval Research and Advanced Research Projects Agency. 9. Archived (PDF) from the original on July 22, 2021.

External links

Oxocarbons
Common oxides
Exotic oxides
Polymers
Compounds derived from oxides


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