Names | |
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Preferred IUPAC name
5-(Cycloprop-2-en-1-ylidene)cyclopenta-1,3-diene | |
Other names
Triapentafulvalene
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Identifiers | |
3D model (
JSmol)
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ChemSpider | |
PubChem
CID
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CompTox Dashboard (
EPA)
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Properties | |
C8H6 | |
Molar mass | 102.136 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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.
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 contains two or more calicene subunits are aromatic, such as trans-bicalicene [2] (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]
Names | |
---|---|
Preferred IUPAC name
5-(Cycloprop-2-en-1-ylidene)cyclopenta-1,3-diene | |
Other names
Triapentafulvalene
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C8H6 | |
Molar mass | 102.136 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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.
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 contains two or more calicene subunits are aromatic, such as trans-bicalicene [2] (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]