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.
ISSN0166-1280.
^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.
ISSN1387-3806.
^Eggerding, David; Robert West (1975). "Synthesis of dihydroxycyclopropenone (deltic acid)". Journal of the American Chemical Society. 97 (1): 207–208.
doi:
10.1021/ja00834a047.
ISSN0002-7863.
^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.
ISSN0002-7863.
^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.
ISSN0040-4020.