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corannulene
Sign in to saveAlso known as [5]circulene, dibenzo[ghi,mno]fluoranthene
Corannulene is a polycyclic aromatic hydrocarbon with chemical formula C20H10. 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.
In the Vinony graph
Within Vinony's link graph, corannulene is referenced by 164 other articles, and connects out to aromaticity, benzo[b]fluoranthene and hydrogen.
It sits within the topics Chembox image size set, Chemical articles with multiple compound IDs and Geodesic polyarenes.
Its subject is documented across 14 Wikipedia language editions.
Chemical data
- Formula
- C20H10
- Molecular weight
- 250.3 g/mol
- IUPAC name
- hexacyclo[11.5.2.04,17.07,16.010,15.014,18]icosa-1(18),2,4(17),5,7(16),8,10(15),11,13,19-decaene
- SMILES
- C1=CC2=C3C4=C1C=CC5=C4C6=C(C=C5)C=CC(=C36)C=C2
- InChIKey
- VXRUJZQPKRBJKH-UHFFFAOYSA-N
- XLogP
- 6
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
Show 3 more facts
- chemical formula
- C₂₀H₁₀
- Commons category
- Corannulene
- canonical SMILES
- C1=CC2=C3C4=C1C=CC5=C4C6=C(C=C5)C=CC(=C36)C=C2
via Wikidata · CC0
~6 min read
Encyclopedic overview
10 sectionsContents
- Synthesis
- Aromaticity
- Reactions
- Reduction
- Photochemistry
- Reaction with electrophiles
- Bicorannulenyl
- Research
- See also
- References
Corannulene is a polycyclic aromatic hydrocarbon with chemical formula C20H10. 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.
==Synthesis== Several synthetic routes exist to corannulene. Flash vacuum pyrolysis techniques generally have lower chemical yields than solution-chemistry syntheses, but offer routes to more derivatives. Corannulene was first isolated in 1966 by multistep organic synthesis. In 1971, the synthesis and properties of corannulane were reported. A flash vacuum pyrolysis method followed in 1991. One synthesis based on solution chemistry consists of a nucleophilic displacement–elimination reaction of an octabromide with sodium hydroxide: 529px|Corannulene synthesis Sygula 2000
Excerpted from Wikipedia’s “corannulene” article, available under the CC BY-SA 4.0 licence.