Calicene

Calicene
Names
IUPAC name
5-(2-Cyclopropen-1-ylidene)-1,3-cyclopentadiene
Identifiers
6249-23-6
3D model (Jmol) Interactive image
ChemSpider 26537418
PubChem 12302244
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 or 5-(2-Cyclopropen-1-ylidene)-1,3-cyclopentadiene is a Fulvalenes 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

  1. Schaad, L. J.; B. Andes Hess , Jr (2001). "Dewar Resonance Energy". Chem. Rev. 101 (5): 1465–1476. doi:10.1021/cr9903609.
  2. 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.
  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.


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