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Cyclobutanetetrone

From Wikipedia, the free encyclopedia
Cyclobutanetetrone
Skeletal formula of cyclobutanetetrone
Skeletal formula of 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 mass112.040 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Cyclobutanetetrone, also calledtetraoxocyclobutane, is anorganic compound[1] with formula C4O4 or (CO)4, the fourfoldketone ofcyclobutane. It would be anoxide of carbon, indeed atetramer ofcarbon 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 bymass spectrometry.[5]

Related compounds

[edit]

Cyclobutanetetrone can be viewed as the neutral counterpart of thesquarateanionC
4
O2−
4
, which is stable and has been known at least since 1959.[6]

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

References

[edit]
  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

[edit]
Common oxides
Exotic oxides
Polymers
Compounds derived from oxides
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