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Corannulene information


Corannulene
Names
IUPAC name
Dibenzo[ghi,mno]fluoranthene[1]
Other names
[5]circulene
Identifiers
CAS Number
  • 5821-51-2 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 10006487 checkY
PubChem CID
  • 11831840
UNII
  • KFD2X7NT86 checkY
CompTox Dashboard (EPA)
  • DTXSID80474164 Edit this at Wikidata
InChI
  • InChI=1S/C20H10/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11(1)16-17(12)19(14)20(15)18(13)16/h1-10H checkY
    Key: VXRUJZQPKRBJKH-UHFFFAOYSA-N checkY
  • InChI=1/C20H10/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11(1)16-17(12)19(14)20(15)18(13)16/h1-10H
    Key: VXRUJZQPKRBJKH-UHFFFAOYAF
SMILES
  • c16ccc2ccc3ccc5c4c(c1c2c34)c(cc5)cc6
  • C1=CC2=CC=C3C=CC4=C5C6=C(C2=C35)C1=CC=C6C=C4
Properties
Chemical formula
C20H10
Molar mass 250.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Corannulene is a polycyclic aromatic hydrocarbon with chemical formula C20H10.[2] The molecule consists of a cyclopentane ring fused with 5 benzene rings, so another name for it is [5]circulene. It is of scientific interest because it is a geodesic polyarene and can be considered a fragment of buckminsterfullerene. Due to this connection and also its bowl shape, corannulene is also known as a buckybowl. Buckybowls are fragments of buckyballs. Corannulene exhibits a bowl-to-bowl inversion with an inversion barrier of 10.2 kcal/mol (42.7 kJ/mol) at −64 °C.[3]

  1. ^ Fluoranthene is so named for its fluorescent property. It is not a fluorine compound.
  2. ^ Scott, L. T.; Bronstein, H. E.; Preda, D. V.; Ansems, R. B. M.; Bratcher, M. S.; Hagen, S. (1999). "Geodesic polyarenes with exposed concave surfaces". Pure and Applied Chemistry. 71 (2): 209. doi:10.1351/pac199971020209. S2CID 37901191.
  3. ^ Scott, L. T.; Hashemi, M. M.; Bratcher, M. S. (1992). "Corannulene bowl-to-bowl inversion is rapid at room temperature". Journal of the American Chemical Society. 114 (5): 1920–1921. doi:10.1021/ja00031a079.

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Corannulene

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Fullerene

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predicted the existence of C 60 in 1970. He noticed that the structure of a corannulene molecule was a subset of the shape of a football, and hypothesised that...

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Hydrocarbon

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Polycyclic aromatic hydrocarbon

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Styrene

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Isobutylene

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Anthracene

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Inherent chirality

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