Misplaced Pages

Cyclopropanetrione

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Cyclopropanetrione
Names
IUPAC name cyclopropane-1,2,3-trione
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3O3/c4-1-2(5)3(1)6Key: RONYDRNIQQTADL-UHFFFAOYSA-N
  • InChI=1/C3O3/c4-1-2(5)3(1)6Key: RONYDRNIQQTADL-UHFFFAOYAP
SMILES
  • O=C1C(=O)C1=O
Properties
Chemical formula C3O3
Molar mass 84.03 g/mol
Related compounds
Related compounds deltic acid oxopropandial
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Cyclopropanetrione or trioxocyclopropane is a little-known oxide of carbon with formula C3O3. It consists of a ring of three carbon atoms each attached to an oxygen atom with a double bond. Alternately, it can be thought as a trimer of carbon monoxide. This compound is predicted to be thermodynamically unstable, dissociating to carbon monoxide, and has not been produced in bulk. However, C3O3 molecules, provisionally assigned to either cyclopropanetrione or its open-chain analog •(CO)3•, have been detected using mass spectrometry.

It is the neutral equivalent of the deltate anion C3O3, known since 1975. An equivalent hydrate hexahydroxycyclopropane or cyclopropane-1,1,2,2,3,3-hexol, (-C(OH)2-)3 also exists. This contains geminal hydroxy groups.

References

  1. Corkran, Greg; David W. Ball (2004). "The relative energies of cyclopropanone, cyclopropanedione, and cyclopropanetrione. Hartree–Fock, density-functional, G2, and CBS calculations". Journal of Molecular Structure: THEOCHEM. 668 (2–3): 171–178. doi:10.1016/j.theochem.2003.10.026. ISSN 0166-1280.
  2. Schröder, Detlef; Helmut Schwarz; Suresh Dua; Stephen J. Blanksby; John H. Bowie (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. ISSN 1387-3806.
  3. Eggerding, David; Robert West (1975). "Synthesis of dihydroxycyclopropenone (deltic acid)". Journal of the American Chemical Society. 97 (1): 207–208. doi:10.1021/ja00834a047. ISSN 0002-7863.
  4. Eggerding, David; Robert West (1976). "Synthesis and properties of deltic acid (dihydroxycyclopropenone) and the deltate ion". Journal of the American Chemical Society. 98 (12): 3641–3644. doi:10.1021/ja00428a043. ISSN 0002-7863.
  5. Skujins, S.; J. Delderfield, G.A. Webb (1968). "A mass spectrometric study of some monocyclic polycarbonyl compounds". Tetrahedron. 24 (13): 4805–4817. doi:10.1016/S0040-4020(01)98676-4. ISSN 0040-4020.
Oxocarbons
Common oxides
Exotic oxides
Polymers
Compounds derived from oxides
Categories: