Chemistry:Sesquifulvalene
| |
| Names | |
|---|---|
| Preferred IUPAC name
7-(Cyclopenta-2,4-dien-1-ylidene)cyclohepta-1,3,5-triene | |
| Other names
Pentaheptafulvalene
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
PubChem CID
|
|
| |
| |
| 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). | |
| Infobox references | |
Sesquifulvalene or pentaheptafulvalene is a hydrocarbon in the fulvalene class with chemical formula C12H10. It is composed of linked cyclopentadiene and cycloheptatriene rings.
Properties
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
References
- ↑ "7-(2,4-Cyclopentadien-1-ylidene)-1,3,5-cycloheptatriene" (in en). https://webbook.nist.gov/cgi/cbook.cgi?Source=1975SCH%2F1099&Mask=400.
- ↑ 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. doi:10.1021/jp3032397. PMID 22536920. Bibcode: 2012JPCA..116.5008D.
 |  |
