Sesquifulvalene

Sesquifulvalene
Names
IUPAC name
7-Cyclopenta-2,4-dien-1-ylidenecyclohepta-1,3,5-triene
Other names
Pentaheptafulvalene
Identifiers
3D model (JSmol)
ChemSpider
Properties
C12H10
Molar mass 154.21 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.[1]

See also

References

  1. ↑ 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": 5008–5017. doi:10.1021/jp3032397.
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