Carbon suboxide

Carbon suboxide

Chembox new
Name = Carbon suboxide
ImageFile = Carbon-suboxide-2D-dimensions.png ImageName = Structure of carbon suboxide
ImageFile1 = Carbon-suboxide-3D-vdW.png 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 = C3O2
MolarMass = 68.0309 g mol−1
Appearance = colorless gas
Density = 0.906 ± 0.06 g/cm3, gas at 298 K
MeltingPt = −107°C
BoilingPt = 6.8°C

Section3 = Chembox Structure
MolShape = linear

Section8 = Chembox Related
Function = oxides
OtherFunctn = carbon dioxide
carbon monoxide
dicarbon monoxide
carbon trioxide
OtherCpds = carbon subnitride

Carbon suboxide, or tricarbon dioxide, C3O2with four cumulative double bonds, making it a cumulene. It is closely related to CO, CO2 and C2O, and other oxides of carbon.

Brodie discovered it in 1873 by submitting electric current to carbon monoxide. [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
] [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
] Marcellin Berthelot created the name carbon suboxide, [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
] 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 (P4O10) and malonic acid or the esters of malonic acid. [cite journal
author = Diels O, Wolf B
title = Ueber das Kohlensuboxyd. I
journal = Chemische Berichte
volume = 39
year = 1906
pages = 689–697
doi = 10.1002/cber.190603901103
] Therefore, it can be also considered as the anhydride of malonic anhydride, i.e. the "second anhydride" of malonic acid. Malonic anhydride (not to be confused with maleic anhydride) is a real molecule. [ [http://www.springerlink.com/content/wx574h4v6513731x/ SpringerLink - Journal Article ] ]

Several other ways for synthesis and reactions of carbon suboxide can be found in a review from 1930 by Reyerson. [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
]

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). [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
] [cite journal
title =The Structure of Carbon Suboxide, C3O2, 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
] In 1969, it was proposed that the color of Martian surface is attributed to this compound, but it was shown to be a incorrect by the Viking mission. [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
]

References

External links

* [http://www.webelements.com/webelements/compounds/text/C/C3O2-504643.html WebElements page on compound's properties]


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