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Calicene
Sign in to saveAlso known as Triapentafulvalene, Pentatriafulvalene, Tripentafulvalene, Pentatrifulvalene
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.
Chemical data
- Formula
- C8H6
- Molecular weight
- 102.13 g/mol
- IUPAC name
- 5-cycloprop-2-en-1-ylidenecyclopenta-1,3-diene
- SMILES
- C1=CC(=C2C=C2)C=C1
- InChIKey
- ZXWMPJFQZJXFQN-UHFFFAOYSA-N
- XLogP
- 2
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 102.04695
Show 2 more facts
- chemical formula
- C₈H₆
- canonical SMILES
- C1=CC(=C2C=C2)C=C1
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Properties
- 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, 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. Several compounds that contain two or more calicene subunits are aromatic, such as trans-bicalicene (ring compound) or poly-2,7-[N]calicenes (chain compound)
Excerpted from Wikipedia’s “Calicene” article, available under the CC BY-SA 4.0 licence.