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Cyclobutanetetrone

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Cyclobutanetetrone
Skeletal formula of cyclobutanetetrone
Names
IUPAC name Cyclobutane-1,2,3,4-tetraone
Other names Tetraoxocyclobutane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4O4/c5-1-2(6)4(8)3(1)7Key: KDAVZOLBYGNLGF-UHFFFAOYSA-N
SMILES
  • O=C1C(=O)C(=O)C1=O
Properties
Chemical formula C4O4
Molar mass 112.040 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Related compounds

Cyclobutanetetrone can be viewed as the neutral counterpart of the squarate anion C
4O
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". 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.
  • Maahs, G.; Hegenberg, P. (2003). "Syntheses and Derivatives of Squaric Acid". Angewandte Chemie International Edition. 5 (10): 888–893. doi:10.1002/anie.196608881.

See also

Oxocarbons
Common oxides
Exotic oxides
Polymers
Compounds derived from oxides
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