Hexaphenylbenzene
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| Names | |
|---|---|
| IUPAC name
1,2,3,4,5,6-hexa(phenyl)benzene | |
| Identifiers | |
992-04-1  | |
| ChemSpider | 63611 |
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| Jmol-3D images | Image |
| PubChem | 70432 |
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| Properties | |
| C42H30 | |
| Molar mass | 534.6876 |
| Melting point | 454 to 456 °C (849 to 853 °F; 727 to 729 K)[1] |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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| Infobox references | |
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.[1]
Structure
Perspective view of the crystal structure of hexaphenylbenzene, showing the rotation of the phenyl rings. Hydrogen atoms have been omitted for clarity.[2]
Due to steric congestion among the phenyl rings, the stable conformation of this molecule has the phenyl rings rotated out of the plane of the central benzene ring. In the crystalline form shown on the left, the molecule forms a propeller-like conformation in which the phenyl rings are rotated about 65°,[2] while in the gas phase, they are perpendicular with some slight oscillations.[3]
References
- ↑ 1.0 1.1 Louis Fieser (1973). "Hexaphenylbenzene". Org. Synth.; Coll. Vol. 5, p. 604
- ↑ 2.0 2.1 Bart, J. C. J. (1968). "The crystal structure of a modification of hexaphenylbenzene". Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry 24 (10): 1277. doi:10.1107/S0567740868004176.
- ↑ Gust, D. (1977). "Restricted Rotation in Hexaarylbenzenes". J. Am. Chem. Soc. 99 (21): 6980–6982. doi:10.1021/ja00463a034.