Carbon suboxide
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2008-06-23T16:21:25Z
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{{Chembox new
| Name = Carbon suboxide
| ImageFile = Carbon-suboxide-2D-dimensions.png
<!-- | ImageSize = 200px -->
| ImageName = Structure of carbon suboxide
| ImageFile1 = Carbon-suboxide-3D-vdW.png
<!-- | ImageSize1 = 200px -->
| ImageName1 = Space-filling model of carbon suboxide
| IUPACName = propadiene-1,3-dione
| Section1 = {{Chembox Identifiers
| CASNo = 504-64-3
| PubChem = 136332
| SMILES = O=C=C=C=O
| InChI = 1/C3O2/c4-2-1-3-5
| ChEBI = 30086
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>3</sub>O<sub>2</sub>
| MolarMass = 68.0309 g mol<sup>−1</sup>
| Appearance = colorless gas
| Density = 0.906 ± 0.06 g/cm<sup>3</sup>, gas at 298 K
| MeltingPt = −107°C
| BoilingPt = 6.8°C
}}
| Section3 = {{Chembox Structure
| MolShape = linear
}}
| Section8 = {{Chembox Related
| Function = oxides
| OtherFunctn = [[carbon dioxide]]<br />[[carbon monoxide]]<br />[[dicarbon monoxide]]<br />[[carbon trioxide]]
| OtherCpds = [[carbon subnitride]]}}
}}
'''Carbon suboxide''', or tricarbon dioxide, C<sub>3</sub>O<sub>2</sub>, is a colorless pungent gas, with four cumulative double bonds, making it a [[cumulene]]. It is closely related to [[carbon monoxide|CO]], [[carbon dioxide|CO<sub>2</sub>]] and [[dicarbon monoxide|C<sub>2</sub>O]], and other [[oxides]] of [[carbon]].
Brodie discovered it in 1873 by submitting electric current to [[carbon monoxide]].<ref>{{cite journal
| author = Brodie B. C.
| title = Note on the Synthesis of Marsh-Gas and Formic Acid, and on the Electric Decomposition of Carbonic Oxide
| journal = Proceedings of the Royal Society (London)
| volume = 21
| year = 1873
| pages = 245–247
|url = http://links.jstor.org/sici?sici=0370-1662%281872%2F1873%2921%3C245%3ANOTSOM%3E2.0.CO%3B2-J
| doi = 10.1098/rspl.1872.0052 }}</ref><ref>{{cite journal
| author = Brodie B. C.
| title = Über eine Synthese von Sumpfgas und Ameisensäure und die electrische Zersetzung des Kohlenoxyds
| journal = [[Annalen der Chemie]]
| volume = 169
| year = 1873
| pages = 270
|doi = 10.1002/jlac.18731690119}}</ref> [[Marcellin Berthelot]] created the name carbon suboxide,
<ref>{{cite journal
| author = [[Marcellin Berthelot]]
| title = Action de la chaleur sur l'oxyde de carbone
| journal = [[Annales de chimie et de physique]]
| volume = 6
| issue = 24
| year = 1891
| pages = 126–132
| url = http://gallica.bnf.fr/ark:/12148/bpt6k34894x/f124.table }}</ref>
while [[Otto Diels]] later stated that the more organic names dicarbonyl methane and dioxallene were also correct.
It is synthesized by warming a dry mixture of [[phosphorus pentoxide]] (P<sub>4</sub>O<sub>10</sub>) and [[malonic acid]] or the [[ester]]s of [[malonic acid]].<ref>{{cite journal
| author = [[Otto Diels|Diels O]], Wolf B
| title = Ueber das Kohlensuboxyd. I
| journal = [[Chemische Berichte]]
| volume = 39
| year = 1906
| pages = 689–697
| doi = 10.1002/cber.190603901103}}</ref>
Therefore, it can be also considered as the anhydride of [[malonic anhydride]], i.e. the "second anhydride" of malonic acid. Malonic anhydride (not the be confused with [[maleic anhydride]]) is a real molecule.<ref>[http://www.springerlink.com/content/wx574h4v6513731x/ SpringerLink - Journal Article<!-- Bot generated title -->]</ref>
Several other ways for synthesis and reactions of carbon suboxide can be found in a review from 1930 by Reyerson.<ref>{{cite journal
| author= Reyerson L. H., Kobe K.
| title= Carbon Suboxide
| journal= [[Chemical Reviews]]
| volume= 7
| year= 1930
| pages= 479–492
| doi =10.1021/cr60028a002}}</ref>
Carbon suboxide polymerizes spontaneously to a red, yellow, or black solid. The structure is postulated to be poly(α-pyronic), similar to the structure in [[2-Pyrone]] (α-Pyrone).
<ref>
{{cite journal
| title = Analysis of Poly(carbon suboxide) by Small-Angle X-ray Scattering
| author = M. Ballauff, L. Li, S. Rosenfeldt, N. Dingenouts, J. Beck, P. Krieger-Beck
| volume = 116
| journal = [[Angewandte Chemie International Edition]]
| issue = 43
| pages =5843–5846
| year = 2004
| doi= 10.1002/anie.200460263}}</ref><ref>{{cite journal
| title =The Structure of Carbon Suboxide, C<sub>3</sub>O<sub>2</sub>, in the Solid State
| author =A. Ellern, T. Drews, K. Seppelt
| journal = Zeitschrift für anorganische und allgemeine Chemie
| volume = 627
| issue = 1
| pages = 73–76
| doi= 10.1002/1521-3749(200101)627:1<73::AID-ZAAC73>3.0.CO;2-A
| year =2001}}</ref>
In 1969, it was proposed that the color of Martian surface is attributed to this compound, but it was proven to be a wrong concept after the Viking mission.<ref>{{cite journal
| author = William T. Plummer & Robert K. Carsont
| title =Mars: Is the Surface Colored by Carbon Suboxide?
| journal = Science
| volume = 166
| pages = 1141
| year = 1969
| doi= DOI
| doi_brokendate =2008-06-23
| unused_data =|10.1126/science.166.3909.1141}}</ref>
==References==
<div class="references-small">
<references/>
</div>
==External links==
*[http://www.webelements.com/webelements/compounds/text/C/C3O2-504643.html WebElements page on compound's properties]
{{Oxides of carbon}}
[[Category:Oxides]]
[[Category:Inorganic carbon compounds]]
{{inorganic-compound-stub}}
[[de:Kohlenstoffsuboxid]]
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[[ko:아산화 탄소]]
[[ja:亜酸化炭素]]
[[pl:Podtlenek węgla]]
[[ru:Диоксид триуглерода]]
[[sr:Угљеник субоксид]]
[[zh:二氧化三碳]]