Global InformationFluorenylidene information
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| Preferred IUPAC name
9H-Fluoren-9-ylidene | |
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CAS Number
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties | |
Chemical formula
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C13H8 |
| Molar mass | 164.207 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
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9-Fluorenylidene is an aryl carbene derived from the bridging methylene group of fluorene. Fluorenylidene has the unusual property that the triplet ground state is only 1.1 kcal/mol (4.6 kJ/mol) lower in energy than the singlet state.[1] For this reason, fluorenylidene has been studied extensively in organic chemistry.
Fluorenylidene is a reactive intermediate. Reactions involving fluorenylidene proceed through either the triplet or singlet state carbene, and the products formed depend on the relative concentration of spin states in solution, as influenced by experimental conditions.[2] The rate of intersystem crossing is determined by the temperature and concentration of specific spin-trapping agents.[1]
- ^ a b Grasse, P. B.; Brauer, B. E.; Zupancic, J. J.; Kaufmann, K. J.; Schuster, G. B. (1983). "Chemical and physical properties of fluorenylidene: equilibration of the singlet and triplet carbenes". Journal of the American Chemical Society. 105 (23): 6833. doi:10.1021/ja00361a014.
- ^ Sitzmann, E. V.; Langan, J. & Eisenthal, K. B. (1984). "Intermolecular effects on intersystem crossing studied on the picosecond timescale: the solvent polarity effect on the rate of singlet-to-triplet intersystem crossing of diphenylcarbene". Journal of the American Chemical Society. 106 (6): 1868–1869. doi:10.1021/ja00318a069.