Carbon suboxide 2208893 221223859 2008-06-23T16:21:25Z DOI bot 6652755 Citation maintenance. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{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]] [[el:Υποξείδιο του άνθρακα]] [[ko:아산화 탄소]] [[ja:亜酸化炭素]] [[pl:Podtlenek węgla]] [[ru:Диоксид триуглерода]] [[sr:Угљеник субоксид]] [[zh:二氧化三碳]]