Cyclobutanetetrone

Cyclobutanetetrone

Skeletal formula of cyclobutanetetrone
Names
IUPAC name Cyclobutane-1,2,3,4-tetraone[ citation needed ]
Other names Tetraoxocyclobutane
Identifiers
CAS Number	76719-54-5  N
3D model (JSmol)	Interactive image
ChemSpider	24735246  Y
PubChem CID	5488007
CompTox Dashboard (EPA)	DTXSID10420518
InChI InChI=1S/C4O4/c5-1-2(6)4(8)3(1)7 Y Key: KDAVZOLBYGNLGF-UHFFFAOYSA-N Y
SMILES O=C1C(=O)C(=O)C1=O
Properties
Chemical formula	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). N  verify  (what is  YN ?) Infobox references

Cyclobutanetetrone, also called tetraoxocyclobutane, is an organic compound ^[1] 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. ^[2] As of 2000 ^[update] , it had yet to be synthesized in significant amounts ^{[3] [4]} but may have transient existence as detected by mass spectrometry. ^[5]

Related compounds

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. ^[6]

The compound octahydroxycyclobutane or cyclobutaneoctaol (C(OH)₂)₄ may be referred to in the literature as "hydrated tetraoxocyclobutane". ^[7]

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 C_nO_n (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

• Cyclohexanehexone
• Cyclopentanepentone