Tetracarbon dioxide

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Tetracarbon dioxide
Full structural formula of tetracarbon dioxide
Space-filling model of the tetracarbon dioxide molecule
Names
IUPAC name
1,4-Butatrienedione
Identifiers
51799-35-0 N
ChemSpider 19001756 N
Jmol 3D model Interactive image
Properties
C4O2
Molar mass 80.042
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tetracarbon dioxide is an oxide of carbon, a chemical compound of carbon and oxygen, with chemical formula C4O2 or O=C=C=C=C=O. It can be regarded as butatriene dione, the double ketone of butatriene — more precisely 1,2,3-butatriene-1,4-dione.[1]

Butatriene dione is the fourth member of the family of linear carbon dioxides O(=C)n=O, that includes carbon dioxide CO2 or O=C=O, ethylene dione C2O2 or O=C=C=O, carbon suboxide C3O2 or O=C=C=C=O, pentacarbon dioxide C5O2 or O=C=C=C=C=C=O, and so on.

The compound was obtained in 1990 by Maier and others, by flash vacuum pyrolysis of cyclic azaketones in a frozen argon matrix.[2] It was also obtained in the same year by Sülzle and Schwartz through impact ionization of ((CH3-)2(C4O2)(=O)2=)2 in the gas phase.[3] Although theoretical studies indicated that the even-numbered members of the O(=C)n=O family should be inherently unstable,[4] C4O2 is indefinitely stable in the matrix, but is decomposed by light into tricarbon monoxide C3O and carbon monoxide CO.[2][1] It has a triplet ground state.[1]

References

  1. 1.0 1.1 1.2 J.I.G. Codagan, John Buckingham, Finlay J. MacDonald, P. H. Rhodes (1996), Dictionary of Organic Compounds. CRC Press, ISBN 0-412-54090-8, ISBN 978-0-412-54090-5. 9000 pages.
  2. 2.0 2.1 Günther Maier, Hans Peter Reisenauer, Heinz Balli, Willy Brandt, Rudolf Janoschek(1990), C4O2 (1,2,3-Butatriene-1,4-dione), the First Dioxide of Carbon with an Even Number of C Atoms. Angewandte Chemie Int. Ed., volume 29, p. 905–908.
  3. Detlev Sülzle, Helmut Schwartz (1990), Identification of Butatrienedione, Its Radical Anion, and Its Radical Cation in the Gas Phase. Angewandte Chemie Int. Ed., volume 29, p. 908–909.
  4. V. Krishnamurthy and V. H. Rawal (1997), J. Org. Chem., volume 62, 1572.
  • François Diederich and Yves Rubin (2003), Synthetic Approaches toward Molecular and Polymeric Carbon Allotropes. Angewandte Chemie Int. Ed., Volume 31 Issue 9, Pages 1101–1123.