Calicene
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| Names | |
|---|---|
| IUPAC name
5-(2-Cyclopropen-1-ylidene)-1,3-cyclopentadiene | |
| Other names
Triapentafulvalene | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| Properties | |
| C8H6 | |
| Molar mass | 102.14 g·mol−1 |
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 fulvalene hydrocarbon with chemical formula C8H6, composed of linked a cyclopentadiene ring and a cyclopropene ring.
Properties
Very high resonance energy is predicted by 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. Calicene's dipole moment is 4.66D.[2] Several compounds that contains two or more calicene subunits are aromatic, such as trans-bicalicene[2](ring compound) or poly-2,7-[N]calicenes (chain compound)[3]
See also
References
- ↑ Schaad, L. J.; B. Andes Hess , Jr (2001). "Dewar Resonance Energy". Chem. Rev. 101 (5): 1465–1476. doi:10.1021/cr9903609.
- 1 2 Oziminski, W. P.; M. Palusia (2013). "Capturing the elusive aromaticity of bicalicene". Phys. Chem. Chem. Phys. 15: 3286–3293. doi:10.1039/C2CP43426A.
- ↑ 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.
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