Hexaphenylbenzene
Appearance
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Names | |
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Preferred IUPAC name
23,24,25,26-Tetraphenyl-11,21:22,31-terphenyl | |
Other names
Hexaphenylbenzene
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.012.356 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C42H30 | |
Molar mass | 534.702 g·mol−1 |
Appearance | white solid |
Melting point | 454 to 456 °C (849 to 853 °F; 727 to 729 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hexaphenylbenzene is an
phenyl rings. It is a colorless solid. The compound is the parent member of a wider class of hexaarylbenzenes, which are mainly of theoretical interest.[2]
Preparation
It is prepared by heating
Diels-Alder reaction to give the hexaphenyldienone, which then eliminates carbon monoxide.[1]
Together with 1,2,3,4-tetraphenylnaphthalene, hexaphenylbenzene forms by the chromium-catalyzed oligomerization of diphenylacetylene.[3] It may also be prepared by the dicobalt octacarbonyl-catalyzed alkyne trimerisation of diphenylacetylene.[2]
Structure
![](http://upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Hexaphenylbenzene_xtal_perspective.png/220px-Hexaphenylbenzene_xtal_perspective.png)
The stable conformation of this molecule has the phenyl rings rotated out of the plane of the central benzene ring. The molecule adopts a propeller-like conformation in which the phenyl rings are rotated about 65°,[4] while in the gas phase, they are perpendicular with some slight oscillations.[5]
References
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- ^ PMID 27498592.)
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