Cyclopropenone

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Cyclopropenone
Cyclopropenone.svg
Names
IUPAC name
2-Cyclopropen-1-one
Other names
Cyclopropenone, Cyclopropene-3-one
Identifiers
3D model (JSmol)
ChemSpider
Properties
C3H2O
Molar mass 54.05 g·mol−1
Appearance colorless liquid
Melting point −29 to −28 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cyclopropenone is an organic compound with molecular formula C3H2O consisting of a cyclopropene carbon framework with a ketone functional group. It is a colorless, volatile liquid that boils near room temperature.[1] Neat cyclopropenone polymerizes upon standing at room temperature.[2] The chemical properties of the compound are dominated by the strong polarization of the carbonyl group, which gives a partial positive charge with aromatic stabilization on the ring and a partial negative charge on oxygen. It is an aromatic compound.[3][4]

Main resonance structures of cyclopropenone.

See also[edit]

References[edit]

  1. ^ R. Breslow, J. Pecoraro, T. Sugimoto "Cyclpropenone" Org. Synth. 1977, vol. 57, pp. 41. doi:10.15227/orgsyn.057.0041
  2. ^ Breslow, Ronald; Oda, Masaji (1972-06-01). "Isolation and characterization of pure cyclopropenone". Journal of the American Chemical Society. 94 (13): 4787–4788. doi:10.1021/ja00768a089. ISSN 0002-7863.
  3. ^ "Experiments show cyclopropenone is aromatic". Chem. Eng. News. 61 (38): 33. 1983. doi:10.1021/cen-v061n038.p033.
  4. ^ Peart, Patricia A.; Tovar, John D. (2010). "Poly(cyclopropenone)s: Formal Inclusion of the Smallest Hückel Aromatic into π-Conjugated Polymers". J. Org. Chem. 76 (15): 5689–5696. doi:10.1021/jo101108f.