Cyclopropenone: Difference between revisions
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'''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> 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 |first1= |last1= |first2= |last2= |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]] 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> 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 |first1= |last1= |first2= |last2= |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> |
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[[File:C3H2OResonance.png|thumb|left|Main resonance structures of cyclopropenone.]] |
[[File:C3H2OResonance.png|thumb|left|Main resonance structures of cyclopropenone.]] |
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== See also == |
== See also == |
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*[[Diphenylcyclopropenone]] |
*[[Diphenylcyclopropenone]] |
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*[[Deltic acid]] |
*[[Deltic acid]] |
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*[[Tropone]] |
*[[Tropone]] |
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==References== |
==References== |
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{{reflist}} |
{{reflist}} |
Revision as of 04:44, 11 November 2017
Names | |
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IUPAC name
2-Cyclopropen-1-one
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Other names
Cyclopropenone, Cyclopropene-3-one
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C3H2O | |
Molar mass | 54.048 g·mol−1 |
Appearance | colorless gas |
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).
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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] 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.[2][3]
See also
References
- ^ R. Breslow, J. Pecoraro, T. Sugimoto "Cyclpropenone" Org. Synth. 1977, vol. 57, pp. 41. doi:10.15227/orgsyn.057.0041
- ^ "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.