Cyclopropanetrione

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Cyclopropanetrione
Names


IUPAC name cyclopropane-1,2,3-trione
Identifiers
CAS Number	76719-55-6
3D model (JSmol)	Interactive image
ChemSpider	35786973
PubChem CID	58556001
CompTox Dashboard (EPA)	DTXSID50729390
InChI InChI=1S/C3O3/c4-1-2(5)3(1)6 Key: RONYDRNIQQTADL-UHFFFAOYSA-N InChI=1/C3O3/c4-1-2(5)3(1)6 Key: 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 [77 °F], 100 kPa). Infobox references

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 thermodynamically unstable^[why?]^[how?] and has not been produced in bulk.^[1] However, it has been detected using mass spectrometry.^[2]^[3]

It is the neutral equivalent of the deltate anion C₃O₃²⁻, known since 1975.^[4] An equivalent hydrate hexahydroxycyclopropane or cyclopropane-1,1,2,2,3,3-hexol, (-C(OH)₂-)₃ also exists. This contains geminal hydroxy groups.^[5]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

v t e Oxocarbons
Common oxides	CO CO₂
Exotic oxides	CO₃ CO₄ CO₅ CO₆ C₂O C₂O₂ C₂O₃ C₂O₄ (1,2-Dioxetanedione and 1,3-Dioxetanedione) C₃O C₃O₂ C₃O₃ C₃O₆ C₄O₂ C₄O₄ C₄O₆ C₅O₂ C₅O₅ C₆O₆ (Cyclohexanehexone and Ethylenetetracarboxylic dianhydride) C₈O₈ C₉O₉ C₁₀O₈ C₁₀O₁₀ C₁₂O₆ C₁₂O₉ C₁₂O₁₂
Polymers	Graphite oxide C₃O₂ CO CO₂
Compounds derived from oxides	Metal carbonyls Carbonic acid Bicarbonates Carbonates Polycarbonates (Dicarbonates and Tricarbonates) Peroxydicarbonates

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