Coronene

Coronene (also known as superbenzene and cyclobenzene) is a polycyclic aromatic hydrocarbon (PAH) comprising seven peri-fused benzene rings. Its chemical formula is C
24H
12. It is a yellow material that dissolves in common solvents including benzene, toluene, and dichloromethane. Its solutions emit blue light fluorescence under UV light. It has been used as a solvent probe, similar to pyrene.

Coronene
Names
Preferred IUPAC name
Coronene
Other names
[6]circulene
X1001757-9, superbenzene, cyclobenzene
Identifiers
3D model (JSmol)
658468
ChEBI
ChemSpider
ECHA InfoCard 100.005.348
EC Number
  • 205-881-7
286459
KEGG
UNII
  • InChI=1S/C24H12/c1-2-14-5-6-16-9-11-18-12-10-17-8-7-15-4-3-13(1)19-20(14)22(16)24(18)23(17)21(15)19/h1-12H Y
    Key: VPUGDVKSAQVFFS-UHFFFAOYSA-N Y
  • InChI=1/C24H12/c1-2-14-5-6-16-9-11-18-12-10-17-8-7-15-4-3-13(1)19-20(14)22(16)24(18)23(17)21(15)19/h1-12H
    Key: VPUGDVKSAQVFFS-UHFFFAOYAQ
  • c1cc2ccc3ccc4ccc5ccc6ccc1c7c2c3c4c5c67
Properties
C24H12
Molar mass 300.360 g·mol−1
Appearance Yellow powder
Density 1.371 g/cm3
Melting point 437.3 °C (819.1 °F; 710.5 K)
Boiling point 525 °C (977 °F; 798 K)
0.14 μg/L
Solubility Very soluble: benzene, toluene, hexane,
Chloroform (1 mmol·L−1) and ethers, sparingly soluble in ethanol.
log P 6.05
Band gap 1.7 eV
-243.3·10−6 cm3/mol
Structure
Monoclinic
P21/n
D6h
a = 10.02 Å, b = 4.67 Å, c = 15.60 Å
α = 90°, β = 106.7°, γ = 90°
2
0 D
Thermochemistry
Enthalpy of fusion (ΔfH⦵fus)
 19.2 kJ/mol
Hazards
GHS labelling:
Warning
H371
P260, P264, P270, P309+P311, P405, P501
NFPA 704 (fire diamond)
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

The compound is of theoretical interest to organic chemists because of its aromaticity. It can be described by 20 resonance structures or by a set of three mobile Clar sextets. In the Clar sextet case, the most stable structure for coronene has only the three isolated outer sextets as fully aromatic although superaromaticity would still be possible when these sextets are able to migrate into the next ring.

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