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kekulene
Sign in to saveAlso known as [12]kekulene, cyclo[d.e.d.e.d.e.d.e.d.e.d.e]dodecakisbenzene
Kekulene is a polycyclic aromatic hydrocarbon which consists of 12 fused benzene rings arranged in a circle. It is therefore classified as a [12]-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.
In the Vinony graph
Vinony's link graph records 153 inbound references to kekulene, and connects out to pentene, benzo[b]fluoranthene and mass density.
It sits within the topics Chembox image size set, Polycyclic aromatic hydrocarbons and Substances discovered in the 1970s.
Vinony links it to 15 Wikipedia language editions.
Chemical data
- Formula
- C48H24
- Molecular weight
- 600.7 g/mol
- IUPAC name
- tridecacyclo[26.18.2.03,44.06,43.08,41.011,40.013,38.016,37.018,35.021,34.023,32.026,31.029,46]octatetraconta-1(46),2,4,6,8(41),9,11,13(38),14,16,18(35),19,21(34),22,24,26(31),27,29,32,36,39,42,44,47-tetracosaene
- SMILES
- C1=CC2=CC3=C4C=C2C5=CC6=C(C=CC7=CC8=C(C=C76)C9=CC2=C(C=CC6=C2C=C2C(=C6)C=CC6=C2C=C4C(=C6)C=C3)C=C9C=C8)C=C51
- InChIKey
- TYPKKLUFDMGLAC-UHFFFAOYSA-N
- XLogP
- 15
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- circulene
- Has part
- carbon
- Named after
- August Kekulé
- Mass
- 600.187801
Show 3 more facts
- canonical SMILES
- C1=CC2=CC3=C4C=C2C5=CC6=C(C=CC7=CC8=C(C=C76)C9=CC2=C(C=CC6=C2C=C2C(=C6)C=CC6=C2C=C4C(=C6)C=C3)C=C9C=C8)C=C51
- chemical formula
- C₄₈H₂₄
- Commons category
- Kekulene
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- Geometry and electronic structure
- References
Kekulene is a polycyclic aromatic hydrocarbon which consists of 12 fused benzene rings arranged in a circle. It is therefore classified as a [12]-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.
== Geometry and electronic structure == The nature of the π bonding within the molecule was long debated, as several distinctly different arrangements were possible. The two most significant proposals are the "Clar" configuration, consisting of six benzene-like (aromatic 6 π-electron) rings connected by bridging bonds and vinyl groups in non-aromatic rings, and the "Kekulé" configuration, consisting of two concentric aromatic rings (18 π-electron inner, 30 π-electron outer) linked by radial single bonds.
Excerpted from Wikipedia’s “kekulene” article, available under the CC BY-SA 4.0 licence.