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1 See also  





2 References  














Cyclopropenone






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Cyclopropenone

Main resonance structures of cyclopropenone.

Names
Preferred IUPAC name

Cycloprop-2-en-1-one

Other names

Cyclopropenone, Cyclopropene-3-one

Identifiers

CAS Number

3D model (JSmol)

ChemSpider

PubChem CID

UNII

CompTox Dashboard (EPA)

  • InChI=1S/C3H2O/c4-3-1-2-3/h1-2H

    Key: GGRQLKPIJPFWEZ-UHFFFAOYSA-N

  • InChI=1/C3H2O/c4-3-1-2-3/h1-2H

    Key: GGRQLKPIJPFWEZ-UHFFFAOYAI

  • c1cc1=O

Properties

Chemical formula

C3H2O
Molar mass 54.048 g·mol−1
Appearance Colorless liquid
Melting point −29 to −28 °C (−20 to −18 °F; 244 to 245 K)

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]

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
  • ^ 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.
  • ^ "Experiments show cyclopropenone is aromatic". Chem. Eng. News. 61 (38): 33. 1983. doi:10.1021/cen-v061n038.p033.
  • ^ 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. PMID 20704438.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Cyclopropenone&oldid=1173088090"

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    Enones
    Simple aromatic rings
    Cyclopropenes
    Non-benzenoid aromatic carbocycles
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