Carbon suboxide

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Template:Chembox E number
Carbon suboxide
IUPAC name propadiene-1,3-dione
Identifiers
3D model (JSmol)
ChEBI
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Properties
C3O2
Molar mass 68.0309 g mol−1
Appearance colorless gas
Density 0.906 ± 0.06 g/cm3, gas at 298 K
Melting point
Boiling point
Structure
Molecular shape linear
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


Overview

Carbon suboxide, or tricarbon dioxide, C3O2, is a colorless pungent gas, with 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.[1][2] Marcellin Berthelot created the name carbon suboxide, [3] 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.[4] 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.[5]

Several other ways for synthesis and reactions of carbon suboxide can be found in a review from 1930 by Reyerson.[6]

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). [7][8] In 1969, it was proposed that the color of Martian surface is attributed to this compound, it was proven to be a wrong concept after the Viking mission.[9]

References

  1. Brodie B. C. (1873). "Note on the Synthesis of Marsh-Gas and Formic Acid, and on the Electric Decomposition of Carbonic Oxide". Proceedings of the Royal Society (London). 21: 245–247.
  2. Brodie B. C. (1873). "Über eine Synthese von Sumpfgas und Ameisensäure und die electrische Zersetzung des Kohlenoxyds". Annalen der Chemie. 169: 270. doi:10.1002/jlac.18731690119.
  3. Marcellin Berthelot (1891). "Action de la chaleur sur l'oxyde de carbone". Annales de chimie et de physique. 6 (24): 126–132.
  4. Diels O, Wolf B (1906). "Ueber das Kohlensuboxyd. I". Chemische Berichte. 39: 689–697. doi:10.1002/cber.190603901103.
  5. http://www.springerlink.com/content/wx574h4v6513731x/
  6. Reyerson L. H., Kobe K. (1930). "Carbon Suboxide". Chemical Reviews. 7: 479–492. doi:10.1021/cr60028a002.
  7. M. Ballauff, L. Li, S. Rosenfeldt, N. Dingenouts, J. Beck, P. Krieger-Beck (2004). "Analysis of Poly(carbon suboxide) by Small-Angle X-ray Scattering". Angewandte Chemie International Edition. 116 (43): 5843–5846. doi:10.1002/anie.200460263.
  8. A. Ellern, T. Drews, K. Seppelt. "The Structure of Carbon Suboxide, C3O2, in the Solid State". Zeitschrift für anorganische und allgemeine Chemie. 627 (1): 73–76. doi:10.1002/1521-3749(200101)627:1<73::AID-ZAAC73>3.0.CO;2-A.
  9. William T. Plummer & Robert K. Carsont (1969). "Mars: Is the Surface Colored by Carbon Suboxide?". Science. 166: 1141. doi:DOI Check |doi= value (help). Text "10.1126/science.166.3909.1141" ignored (help)

External links

de:Kohlenstoffsuboxid el:Υποξείδιο του άνθρακα sr:Угљеник субоксид



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