Tetracarbon dioxide: Difference between revisions

{{Chembox

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 385823816

|ImageFile = Tetracarbon dioxide.svg

|ImageSize = 210

|ImageAlt = Full structural formula of tetracarbon dioxide

|ImageFile1 = Tetracarbon dioxide 3D spacefill.png

|ImageSize1 = 210

|ImageAlt1 = Space-filling model of the tetracarbon dioxide molecule

|PIN = Buta-1,2,3-triene-1,4-dione

|CASNo_Ref = {{cascite|correct|ChemSpider}}

|CASNo = 51799-35-0

|PubChem = 15039474

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 19001756

|SMILES = O=C=C=C=C=O

|StdInChI_Ref = {{stdinchicite|correct|PubChem}}

|StdInChI = 1S/C4O2/c5-3-1-2-4-6

|StdInChIKey_Ref = {{stdinchicite|correct|PubChem}}

|StdInChIKey = QIQCZROILFZKAT-UHFFFAOYSA-N

}}

|Formula = C₄O₂

|MolarMass = 80.042

}}

'''Tetracarbon dioxide''' is an [[oxocarbon|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'''.<ref name="coda">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</ref>

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 [[Günther Maier]] and others, by [[flash vacuum pyrolysis]] of cyclic [[azaketone]]s in a [[Matrix isolation|frozen argon matrix]].<ref name="maier"/> It was also obtained in the same year by [[Detlev Sülzle]] and [[Helmut Schwartz]] through [[impact ionization]] of ((CH₃-)₂(C₄O₂)(=O)₂=)₂<!--my guess for the name: bis(2,2-dimethyl-2,6-diketo-1,3-dioxane-5-enyl)--> in the gas phase.<ref>Detlev Sülzle, Helmut Schwartz (1990), ''Identification of Butatrienedione, Its Radical Anion, and Its Radical Cation in the Gas Phase''. Angewandte Chemie International Edition, volume 29, p. 908–909.</ref> Although theoretical studies indicated that the even-numbered members of the O(=C)_''n''=O family should be inherently unstable,<ref>V. Krishnamurthy and V. H. Rawal (1997), J. Org. Chem., volume 62, 1572.</ref> C₄O₂ is indefinitely stable in the matrix, but is decomposed by light into [[tricarbon monoxide]] C₃O and [[carbon monoxide]] CO.<ref name="maier">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 International Edition, volume 29, p. 905–908.</ref><ref name="coda"/> It has a [[Spin triplet|triplet]] ground state.<ref name="coda"/>

* François Diederich and Yves Rubin (2003), ''Synthetic Approaches toward Molecular and Polymeric Carbon Allotropes''. Angewandte Chemie International Edition, Volume 31 Issue 9, Pages 1101–1123.

[[Category:Oxocarbons]]

[[Category:Enones]]

[[Category:Ketenes]]

[[Category:Diketones]]

[[Category:Substances discovered in the 1990s]]

[[Category:Heterocumulenes]]