Cyclopropenone: Difference between revisions

Cyclopropenone
	; Main resonance structures of cyclopropenone.
Names
	Preferred IUPAC name Cycloprop-2-en-1-one
	Other names Cyclopropenone, Cyclopropene-3-one
Identifiers
CAS Number	2961-80-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	121433;
PubChem CID	137779;
UNII	5MPZ6QZ6ZF ;
CompTox Dashboard (EPA)	DTXSID50183796 ;
	InChI 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;
	SMILES 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

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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] 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]

References

^ 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.
^ 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.
^ "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.

[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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@@ Line 1: / Line 1: @@
 {{Chembox
-| ImageFile = Cyclopropenone.svg
+| ImageFile = Cyclopropenone.svg
 | ImageSize = 120px
+| ImageFile1 = C3H2OResonance.png
-| IUPACName = 2-Cyclopropen-1-one
+| ImageFile2 = Cyclopropenone-3D-vdW.png
-| OtherNames = Cyclopropenone, Cyclopropene-3-one
+| ImageCaption1 = Main resonance structures of cyclopropenone.
+| PIN = Cycloprop-2-en-1-one
+| OtherNames = Cyclopropenone, Cyclopropene-3-one
 | 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
+| ChemSpiderID = 121433
-| SMILES =
+| SMILES = c1cc1=O
-| StdInChI=
+| InChI = 1/C3H2O/c4-3-1-2-3/h1-2H
-| StdInChIKey =
+| InChIKey = GGRQLKPIJPFWEZ-UHFFFAOYAI
-  }}
+| StdInChI = 1S/C3H2O/c4-3-1-2-3/h1-2H
+| StdInChIKey = GGRQLKPIJPFWEZ-UHFFFAOYSA-N
+}}
 | Section2 = {{Chembox Properties
 | C=3|H=2|O=1
-| Appearance = colorless gas
+| Appearance = Colorless liquid
+| MeltingPtC = −29 to −28
-| Density =
-| MeltingPt = −29 to −28 °C
-| BoilingPt =
-| Solubility =
-  }}
-| 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 gas.<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.
+'''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>
+== See also ==
-[[File:C3H2OResonance.png|thumb|left|Main resonance structures of cyclopropenone.]]
+*[[Diphenylcyclopropenone]]
+*[[Deltic acid]]
+*[[Tropone]]
 ==References==
 {{reflist}}
 {{Molecules detected in outer space}}
-[[Category:Ketones]]
+[[Category:Enones]]
+[[Category:Simple aromatic rings]]
 [[Category:Cyclopropenes]]
+[[Category:Non-benzenoid aromatic carbocycles]]