Oxalic anhydride

Oxalic anhydride
Names
	Preferred IUPAC name Oxiranedione
	Other names oxalic anhydride; ethanedioic anhydride
Identifiers
CAS Number	308818-63-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	13693079 ;
PubChem CID	23297885;
CompTox Dashboard (EPA)	DTXSID00632683 ;
	InChI InChI=1S/C2O3/c3-1-2(4)5-1 Key: PFPYHYZFFJJQFD-UHFFFAOYSA-N ; InChI=1/C2O3/c3-1-2(4)5-1 Key: PFPYHYZFFJJQFD-UHFFFAOYAE;
	SMILES O=C1OC1=O;
Properties
Chemical formula	C2O3
Molar mass	72.019 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[1]

It has been conjectured to be a fleeting intermediate in the thermal decomposition of certain oxalates^[2] and certain chemoluminescent reactions of oxalyl chloride.^[3]

References

^ 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.
^ 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.
^ 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

Media related to Oxalic anhydride at Wikimedia Commons

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

[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.

[sherif-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.

[rauhut-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.

[1]

[2]

[3]

Names


Preferred IUPAC name Oxiranedione
Other names oxalic anhydride ethanedioic anhydride
Identifiers
CAS Number	308818-63-5^Y
3D model (JSmol)	Interactive image
ChemSpider	13693079^Y
PubChem CID	23297885
CompTox Dashboard (EPA)	DTXSID00632683
InChI InChI=1S/C2O3/c3-1-2(4)5-1^Y Key: PFPYHYZFFJJQFD-UHFFFAOYSA-N^Y InChI=1/C2O3/c3-1-2(4)5-1 Key: PFPYHYZFFJJQFD-UHFFFAOYAE
SMILES O=C1OC1=O
Properties
Chemical formula	C₂O₃
Molar mass	72.019 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Oxalic anhydride

See also

References

External links