Cyclobutanetetrone

Cyclobutanetetrone
Names
IUPAC name
Cyclobutane-1,2,3,4-tetraone[citation needed]
Other names
Tetraoxocyclobutane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4O4/c5-1-2(6)4(8)3(1)7 checkY
    Key: KDAVZOLBYGNLGF-UHFFFAOYSA-N checkY
  • O=C1C(=O)C(=O)C1=O
Properties
C4O4
Molar mass 112.040 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclobutanetetrone, also called tetraoxocyclobutane, is an organic compound with formula C4O4 or (CO)4, the fourfold ketone of cyclobutane. It would be an oxide of carbon, indeed a tetramer of carbon monoxide.

The compound seems to be thermodynamically unstable. As of 2000, it had yet to be synthesized in significant amounts but may have transient existence as detected by mass spectrometry.

Cyclobutanetetrone can be viewed as the neutral counterpart of the squarate anion C
4O2−
4, which is stable and has been known at least since 1959.

The compound octahydroxycyclobutane or cyclobutaneoctaol (C(OH)2)4 may be referred to in the literature as "hydrated tetraoxocyclobutane".

References

  1. ↑ Guo, J.-C.; Hou, G.-L.; Li, S.-D.; Wang, X.-B. (2012). "Probing the Low-Lying Electronic States of Cyclobutanetetraone (C4O4) and Its Radical Anion: A Low-Temperature Anion Photoelectron Spectroscopic Approach". The Journal of Physical Chemistry A. 3 (3): 304–308. doi:10.1021/jz201593z. PMID 26285843.
  2. ↑ Jiao, H.; Frapper, G.; Halet, J.-F.; Saillard, J.-Y. (2001). "Stability of Tetraoxocyclobutane Revised: Perturbation Theory and Density Functional Scheme". Journal of Physical Chemistry Letters. 105 (24): 5945–5947. Bibcode:2001JPCA..105.5945J. doi:10.1021/jp010738i.
  3. ↑ Rubin, M. B.; Gleiter, R. (2000). "The Chemistry of Vicinal Polycarbonyl Compounds". Chemical Reviews. 100 (3): 1121–1164. doi:10.1021/cr960079j. PMID 11749259.
  4. ↑ Seitz, G.; Imming, P. (1992). "Oxocarbons and pseudooxocarbons". Chemical Reviews. 92 (6): 1227–1260. doi:10.1021/cr00014a004.
  5. ↑ Schröder, D.; Schwarz, H.; Dua, S.; Blanksby, S. J.; Bowie, J. H. (1999). "Mass spectrometric studies of the oxocarbons CnOn (n = 3–6)". International Journal of Mass Spectrometry. 188 (1–2): 17–25. Bibcode:1999IJMSp.188...17S. doi:10.1016/S1387-3806(98)14208-2.
  6. ↑ Cohen, S.; Lacher, J. R.; Park, J. D. (1959). "Diketocyclobutanediol". Journal of the American Chemical Society. 81 (13): 3480. doi:10.1021/ja01522a083.
  7. ↑ Skujins, S.; Delderfield, J.; Webb, G. A. (1967). "A mass spectrometric study of some monocyclic polycarbonyl compounds". Tetrahedron. 24 (13): 4805–4817. doi:10.1016/S0040-4020(01)98676-4.

See also