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| ImageFile = Cyclopropenone.svg
| ImageFile = Cyclopropenone.svg
| ImageSize = 120px
| ImageSize = 120px
| ImageFile1 = C3H2OResonance.png
| IUPACName = 2-Cyclopropen-1-one
| ImageFile2 = Cyclopropenone-3D-vdW.png
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| ImageCaption1 = Main resonance structures of cyclopropenone.
| PIN = Cycloprop-2-en-1-one
| OtherNames = Cyclopropenone, Cyclopropene-3-one
| OtherNames = Cyclopropenone, Cyclopropene-3-one
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| CASNo = 2961-80-0
| CASNo = 2961-80-0
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5MPZ6QZ6ZF
| PubChem = 137779
| PubChem = 137779
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| ChemSpiderID = 121433

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| SMILES = c1cc1=O
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| ChemSpiderID = 121433
⚫
| InChI = 1/C3H2O/c4-3-1-2-3/h1-2H
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| SMILES = c1cc1=O
⚫
| InChIKey = GGRQLKPIJPFWEZ-UHFFFAOYAI
⚫
| InChI = 1/C3H2O/c4-3-1-2-3/h1-2H
⚫
| StdInChI = 1S/C3H2O/c4-3-1-2-3/h1-2H
⚫
| InChIKey = GGRQLKPIJPFWEZ-UHFFFAOYAI
⚫
| StdInChIKey = GGRQLKPIJPFWEZ-UHFFFAOYSA-N
⚫
| StdInChI = 1S/C3H2O/c4-3-1-2-3/h1-2H
⚫
}}
⚫
| StdInChIKey = GGRQLKPIJPFWEZ-UHFFFAOYSA-N

⚫
}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| C=3|H=2|O=1
| C=3|H=2|O=1
| Appearance = colorless liquid
| Appearance = Colorless liquid
⚫
| MeltingPtC = −29 to −28
| Density =
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}}
⚫
| MeltingPt = −29 to −28 °C
| BoilingPt =
| Solubility =
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}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
}}
'''Cyclopropenone''' is an [[organic compound]] with [[molecular formula]] C<sub>3</sub>H<sub>2</sub>O consisting of a [[cyclopropene]] carbon framework with a [[ketone]] [[functional group]]. It is a colorless, volatile liquid that boils near room temperature.<ref>R. Breslow, J. Pecoraro, T. Sugimoto "Cyclpropenone" Org. Synth. 1977, vol. 57, pp. 41. {{DOI|10.15227/orgsyn.057.0041}}</ref> Neat cyclopropenone polymerizes upon standing at room temperature.<ref>{{Cite journal|last=Breslow|first=Ronald|last2=Oda|first2=Masaji|date=1972-06-01|title=Isolation and characterization of pure cyclopropenone|journal=Journal of the American Chemical Society|volume=94|issue=13|pages=4787–4788|doi=10.1021/ja00768a089|issn=0002-7863}}</ref> The chemical properties of the compound are dominated by the strong [[dielectric|polarization]] of the [[carbonyl]] group, which gives a partial positive charge with [[aromaticity|aromatic stabilization]] on the ring and a partial negative charge on oxygen. It is an aromatic compound.<ref>{{cite journal |title= Experiments show cyclopropenone is aromatic |journal= Chem. Eng. News |year= 1983 |volume= 61 |issue= 38 |pages= 33 |doi= 10.1021/cen-v061n038.p033 }}</ref><ref>{{cite journal |title= Poly(cyclopropenone)s: Formal Inclusion of the Smallest Hückel Aromatic into π-Conjugated Polymers |first1= Patricia A. |last1= Peart|first2= John D. |last2= Tovar |journal= J. Org. Chem. |year= 2010 |volume= 76 |issue= 15 |pages= 5689–5696 |doi= 10.1021/jo101108f }}</ref>
'''Cyclopropenone''' is an [[organic compound]] with [[molecular formula]] {{chem2|C3H2O}} consisting of a [[cyclopropene]] carbon framework with a [[ketone]] [[functional group]]. It is a colorless, volatile liquid that boils near room temperature.<ref>R. Breslow, J. Pecoraro, T. Sugimoto "Cyclpropenone" Org. Synth. 1977, vol. 57, pp. 41. {{doi|10.15227/orgsyn.057.0041}}</ref> Neat cyclopropenone polymerizes upon standing at room temperature,<ref>{{Cite journal|last1=Breslow|first1=Ronald|last2=Oda|first2=Masaji|date=1972-06-01|title=Isolation and characterization of pure cyclopropenone|journal=Journal of the American Chemical Society|volume=94|issue=13|pages=4787–4788|doi=10.1021/ja00768a089|issn=0002-7863}}</ref> and chemical vendors typically supply it as an [[acetal]].<ref>{{cite encyclopedia|doi=10.1002/047084289X.rn00486|entry=Cyclopropene, 3,3&#x2011;Dimethoxy|first1=Gregory&nbsp;I.|last1=Elliott|first2=Dale&nbsp;L.|last2=Boger|encyclopedia=[[Encyclopedia of Reagents for Organic Synthesis]]|quote=Dimethyl cyclopropenone ketal is less stable than the corresponding cyclic ketal derivatives....A direct route to cyclopropenone is the hydrolysis of 3,3{{nbh}}dimethoxy&shy;cyclopropene.}}</ref> The chemical properties of the compound are dominated by the strong [[dielectric|polarization]] of the [[carbonyl]] group, which gives a partial positive charge with [[aromaticity|aromatic stabilization]] on the ring and a partial negative charge on oxygen. It is an aromatic compound.<ref>{{cite journal |title= Experiments show cyclopropenone is aromatic |journal= Chem. Eng. News |year= 1983 |volume= 61 |issue= 38 |pages= 33 |doi= 10.1021/cen-v061n038.p033 }}</ref><ref>{{cite journal |title= Poly(cyclopropenone)s: Formal Inclusion of the Smallest Hückel Aromatic into π-Conjugated Polymers |first1= Patricia A. |last1= Peart|first2= John D. |last2= Tovar |journal= J. Org. Chem. |year= 2010 |volume= 76 |issue= 15 |pages= 5689–5696 |doi= 10.1021/jo101108f |pmid= 20704438 }}</ref>

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[[File:C3H2OResonance.png|thumb|left|Main resonance structures of cyclopropenone.]]


== See also ==
== See also ==

Latest revision as of 22:31, 16 June 2024

Cyclopropenone

Main resonance structures of cyclopropenone.
Names
Preferred IUPAC name
Cycloprop-2-en-1-one
Other names
Cyclopropenone, Cyclopropene-3-one
Identifiers
3D model (JSmol)
ChemSpider
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
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).

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. It is an aromatic compound.[4][5]

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. ^ Elliott, Gregory I.; Boger, Dale L. "Cyclopropene, 3,3‑Dimethoxy". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00486. 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.
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