Cyclobutanetetrone
| Cyclobutanetetrone | |
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Cyclobutane-1,2,3,4-tetraone[citation needed] |
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Other names
Tetraoxocyclobutane |
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| Identifiers | |
| CAS number | 3617-57-0  |
| ChemSpider | 24735246  |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4O4 |
| Molar mass | 112.04 g mol−1 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Cyclobutanetetrone, also called tetraoxocyclobutane, is an organic compound[1] with formula C4O4 or (-(C=O)-)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, it had yet to be synthesized in significant amounts[3][4] but may have transient existence as detected by mass spectrometry.[5]
Related compounds[edit]
Cyclobutanetetrone can be viewed as the neutral counterpart of the squarate anion C4O42−, which is stable and has been known at least since 1959.[6]
The compound octahydroxycyclobutane or cyclobutane-1,1,2,2,3,3,4,4-octaol (-C(OH)2-)4 may be referred to in the literature as "hydrated tetraoxocyclobutane".[7]
References[edit]
- ^ 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.
- ^ 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. doi:10.1021/jp010738i.
- ^ Rubin, M. B.; Gleiter, R. (2000). "The Chemistry of Vicinal Polycarbonyl Compounds". Chemical Reviews 100 (3): 1121–1164. doi:10.1021/cr960079j. PMID 11749259.
- ^ Seitz, G.; Imming, P. (1992). "Oxocarbons and pseudooxocarbons". Chemical Reviews 92 (6): 1227–1260. doi:10.1021/cr00014a004.
- ^ 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. doi:10.1016/S1387-3806(98)14208-2.
- ^ Cohen, S.; Lacher, J. R.; Park, J. D. (1959). "Diketocyclobutanediol". Journal of the American Chemical Society 81 (13): 3480. doi:10.1021/ja01522a083.
- ^ 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[edit]
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