Calicene

Calicene
	source ↗
Names
	Preferred IUPAC name 5-(Cycloprop-2-en-1-ylidene)cyclopenta-1,3-diene
	Other names Triapentafulvalene
Identifiers
CAS Number	6249-23-6;
3D model (JSmol)	Interactive image;
ChemSpider	26537418;
PubChem CID	12302244;
CompTox Dashboard (EPA)	DTXSID60486629 ;
	InChI InChI=1S/C8H6/c1-2-4-7(3-1)8-5-6-8/h1-6H Key: ZXWMPJFQZJXFQN-UHFFFAOYSA-N;
	SMILES C1(C=CC=C1)=C2C=C2;
Properties
Chemical formula	C8H6
Molar mass	102.136 g·mol−1
Solubility in water	none in water
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Calicene or triapentafulvalene is a hydrocarbon of the fulvalene class with chemical formula C₈H₆, composed of a cyclopentadiene ring and a cyclopropene ring linked by a double bond. Its name is derived from the Latin calix meaning "goblet", from its shape.

Properties

Very high resonance energy is predicted by the Hückel method,¹ however its resonance energy is not high. The central double bond is polarized with a partial positive charge on the carbon atom of triangular ring and a partial negative charge on the carbon atom of pentagonal ring, in keeping with added Hückel's rule stability of rings containing 2 π electrons and 6 π electrons respectively. Calicene's dipole moment has been computed to be 4.66 D.² Several compounds that contain two or more calicene subunits are aromatic, such as trans-bicalicene² (ring compound) or poly-2,7-[N]calicenes (chain compound)³

Despite several attempts to prepare it, the parent calicene has so far defied attempts at synthesis.⁴ However, 1,2,3,4,5,6-hexaphenylcalicene has been prepared and an experimental dipole moment of 6.3 D was measured.⁵

References

Schaad, L. J.; B. Andes Hess, Jr (2001). "Dewar Resonance Energy". Chemical Reviews. 101 (5): 1465–1476. doi:10.1021/cr9903609. PMID 11710229.
Oziminski, W. P.; M. Palusia (2013). "Capturing the elusive aromaticity of bicalicene". Physical Chemistry Chemical Physics. 15 (9): 3286–3293. Bibcode:2013PCCP...15.3286O. doi:10.1039/C2CP43426A. hdl:11370/73e4cb3f-6c3c-4e9d-b72e-6043b01680c0. PMID 23358331.
Ratanadachanakin, Thawalrat; Collier, Willard E. R. (2015). "Aromaticity of a series of poly-2,7-[N]calicenes" (PDF). Maejo International Journal of Science and Technology. 9 (1): 21–31.
de Meijere, Armin (2014). Houben-Weyl Methods of Organic Chemistry Vol. E 17d, 4th Edition Supplement: Carbocyclic Three-Membered Ring Compounds, Cyclopropenes, Author Index, Compound Index. Stuttgart: Georg Thieme Verlag. p. 2967. ISBN 978-3131819741.
Agranat, Israel; Bergmann, Ernst D. (1965-01-01). "Hexaphenyltriapentafulvalene". Chemical Communications (21): 512–513. doi:10.1039/C19650000512. ISSN 0009-241X.

[1] Schaad, L. J.; B. Andes Hess, Jr (2001). "Dewar Resonance Energy". Chemical Reviews. 101 (5): 1465–1476. doi:10.1021/cr9903609. PMID 11710229.

[bicalicene-2] Oziminski, W. P.; M. Palusia (2013). "Capturing the elusive aromaticity of bicalicene". Physical Chemistry Chemical Physics. 15 (9): 3286–3293. Bibcode:2013PCCP...15.3286O. doi:10.1039/C2CP43426A. hdl:11370/73e4cb3f-6c3c-4e9d-b72e-6043b01680c0. PMID 23358331.

[3] Ratanadachanakin, Thawalrat; Collier, Willard E. R. (2015). "Aromaticity of a series of poly-2,7-[N]calicenes" (PDF). Maejo International Journal of Science and Technology. 9 (1): 21–31.

[4] Meijere, Armin (2014). Houben-Weyl Methods of Organic Chemistry Vol. E 17d, 4th Edition Supplement: Carbocyclic Three-Membered Ring Compounds, Cyclopropenes, Author Index, Compound Index. Stuttgart: Georg Thieme Verlag. p. 2967. ISBN 978-3131819741.

[5] Agranat, Israel; Bergmann, Ernst D. (1965-01-01). "Hexaphenyltriapentafulvalene". Chemical Communications (21): 512–513. doi:10.1039/C19650000512. ISSN 0009-241X.

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