Kekulene

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Kekulene
Skeletal formula of kekulene
Space-filling model of the kekulene molecule
Kekulene-3D-balls.png
Names
Other names
[12]–Coronaphen
Identifiers
15123-47-4 YesY
ChEBI CHEBI:32987 N
ChemSpider 4574217 N
Jmol-3D images Image
PubChem 5460755
Properties
C48H24
Molar mass 600.72 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Kekulene is a polycyclic aromatic hydrocarbon and a circulene with the chemical formula C48H24. It was first synthesized in 1978, and was named in honor of August Kekulé, the discoverer of the structure of the benzene molecule.

References[edit]

  • Peter, R.; Jenny, W. (1966). "250. Höhere, kondensierte Ringsysteme. 1. Mitteilung [1]: Untersuchungen in der [10]-Coronaphenreihe: Synthese von Di-[benzo(c)phenanthren-3, 10-dimethylen]". Helvetica Chimica Acta 49 (7): 2123. doi:10.1002/hlca.660490717. 
  • Staab, Heinz A.; Diederich, François (1983). "Cycloarenes, a New Class of Aromatic Compounds, I. Synthesis of Kekulene". Chemische Berichte 116 (10): 3487. doi:10.1002/cber.19831161021. 
  • Krieger, Claus; Diederich, Francois; Schweitzer, Dieter; Staab, Heinz A. (1979). "Molecular Structure and Spectroscopic Properties of Kekulene". Angewandte Chemie International Edition in English 18 (9): 699. doi:10.1002/anie.197906991. 
  • Aihara, Junichi (1992). "Is superaromaticity a fact or an artifact? The kekulene problem". Journal of the American Chemical Society 114 (3): 865. doi:10.1021/ja00029a009. 
  • Diederich, François; Staab, Heinz A. (1978). "Benzenoidversus Annulenoid Aromaticity: Synthesis and Properties of Kekulene". Angewandte Chemie International Edition in English 17 (5): 372. doi:10.1002/anie.197803721. 
  • Jiao, Haijun; Schleyer, Paul von Ragué (1996). "Is Kekulene Really Superaromatic?". Angewandte Chemie International Edition in English 35 (20): 2383. doi:10.1002/anie.199623831. 
  • Schweitzer, D.; Hausser, K.H.; Vogler, H.; Diederich, F.; Staab, H.A. (1982). "Electronic properties of kekulene". Molecular Physics 46 (5): 1141. doi:10.1080/00268978200101861. 
  • Cioslowski, Jerzy; O'Connor, Peter B.; Fleischmann, Eugene D. (1991). "Is superbenzene superaromatic?". Journal of the American Chemical Society 113 (4): 1086. doi:10.1021/ja00004a005. 
  • Staab, Heinz A.; Diederich, FrançOis; Krieger, Claus; Schweitzer, Dieter (1983). "Cycloarenes, a New Class of Aromatic Compounds, II. Molecular Structure and Spectroscopic Properties of Kekulene". Chemische Berichte 116 (10): 3504. doi:10.1002/cber.19831161022. 
  • Zhou, Zhongxiang (1995). "Are kekulene, coronene, and corannulene tetraanion superaromatic? Theoretical examination using hardness indices". Journal of Physical Organic Chemistry 8 (2): 103. doi:10.1002/poc.610080209.