Sesquifulvalene
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| Names | |
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| Preferred IUPAC name
7-(Cyclopenta-2,4-dien-1-ylidene)cyclohepta-1,3,5-triene | |
| Other names
Pentaheptafulvalene
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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 | |
| C12H10 | |
| Molar mass | 154.212 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sesquifulvalene or pentaheptafulvalene is a hydrocarbon in the fulvalene class with chemical formula C12H10. It is composed of linked cyclopentadiene and cycloheptatriene rings.
Properties
[edit]In the ground state, which is a singlet state, the central double bond is polarized, with a partial positive charge on the carbon atom of heptagonal ring and a partial negative charge on the carbon atom of pentagonal ring. This shift makes each ring have closer to 4n+2 π electrons, in keeping with the Hückel's pattern of aromatic stability. However, in the lowest quintet state, the central double bond is polarized with a partial negative charge on the carbon atom of heptagonal ring and a partial positive charge on the carbon atom of pentagonal ring due to Baird's rule.[2]
See also
[edit]References
[edit]- ^ "7-(2,4-Cyclopentadien-1-ylidene)-1,3,5-cycloheptatriene". webbook.nist.gov.
- ^ Christian Dahlstrand; Martin Rosenberg (2012). "Exploration of the π-Electronic Structure of Singlet, Triplet, and Quintet States of Fulvenes and Fulvalenes Using the Electron Localization Function". The Journal of Physical Chemistry A. 116 (20): 5008–5017. Bibcode:2012JPCA..116.5008D. doi:10.1021/jp3032397. PMID 22536920.
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