Cyclopropenone

Last updated
Cyclopropenone
Cyclopropenone.svg
Cyclopropenone-3D-vdW.png
Names
Preferred IUPAC name
Cycloprop-2-en-1-one
Other names
Cyclopropenone, Cyclopropene-3-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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
C3H2O
Molar mass 54.048 g·mol−1
AppearanceColorless 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).

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] and chemical vendors typically supply it as an acetal. [3] 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. [4] [5]

Main resonance structures of cyclopropenone C3H2OResonance.png
Main resonance structures of cyclopropenone

Cyclopropenone has been observed in the gas phase in interstellar environments such as the Taurus molecular cloud. [6]

See also

References

  1. ↑ "Cyclopropenone". Organic Syntheses. 57: 41. 1977. 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. Bibcode:1972JAChS..94.4787B. doi:10.1021/ja00768a089. ISSN   0002-7863.
  3. ↑ Elliott, Gregory I.; Boger, Dale L. (2004). "Cyclopropene, 3,3‑Dimethoxy". Cyclopropene, 3,3-Dimethoxy. Encyclopedia of Reagents for Organic Synthesis . doi:10.1002/047084289X.rn00486. ISBN   0-471-93623-5. Dimethyl cyclopropenone ketal is less stable than the corresponding cyclic ketal derivatives....A direct route to cyclopropenone is the hydrolysis of 3,3‑dimethoxy­cyclopropene.
  4. ↑ "Experiments show cyclopropenone is aromatic". Chem. Eng. News. 61 (38): 33. 1983. doi:10.1021/cen-v061n038.p033.
  5. ↑ 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.
  6. ↑ Hollis, J. M.; Remijan, Anthony J.; Jewell, P. R.; Lovas, F. J. (2006-05-10). "Cyclopropenone (c-H 2 C 3 O): A New Interstellar Ring Molecule". The Astrophysical Journal. 642 (2): 933–939. doi:10.1086/501121. ISSN   0004-637X.
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