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Hexaphenylbenzene

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Hexaphenylbenzene
Names
IUPAC name 1,2,3,4,5,6-hexa(phenyl)benzene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.356 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C42H30/c1-7-19-31(20-8-1)37-38(32-21-9-2-10-22-32)40(34-25-13-4-14-26-34)42(36-29-17-6-18-30-36)41(35-27-15-5-16-28-35)39(37)33-23-11-3-12-24-33/h1-30HKey: QBHWPVJPWQGYDS-UHFFFAOYSA-N
  • InChI=1/C42H30/c1-7-19-31(20-8-1)37-38(32-21-9-2-10-22-32)40(34-25-13-4-14-26-34)42(36-29-17-6-18-30-36)41(35-27-15-5-16-28-35)39(37)33-23-11-3-12-24-33/h1-30HKey: QBHWPVJPWQGYDS-UHFFFAOYAG
SMILES
  • c1cc(ccc1)c3c(c(c(c(c3c2ccccc2)c4ccccc4)c5ccccc5)c6ccccc6)c7ccccc7
Properties
Chemical formula C42H30
Molar mass 534.6876
Melting point 454-456 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Hexaphenylbenzene is an aromatic compound composed of a benzene ring substituted with six phenyl rings.

It may be prepared through a Diels-Alder reaction by refluxing tetraphenylcyclopentadienone and diphenylacetylene in benzophenone or other high-temperature solvent.

Hexaphenylbenzene synthesis

Due to steric congestion among the phenyl rings, the stable conformation of this molecule has these rings rotated out of the plane of the central benzene ring. In the crystalline form, molecule forms a propeller-like conformation in which the phenyl rings are rotated about 65°, while in the gas phase, they are perpendicular with some slight oscillations.

References

  1. ^ Louis Fieser (1973). "Hexaphenylbenzene". Organic Syntheses; Collected Volumes, vol. 5, p. 604.
  2. Gust, D. (1977). "Restricted Rotation in Hexaarylbenzenes". J. Am. Chem. Soc. 99 (21): 6980–6982. doi:10.1021/ja00463a034.
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