Hexaphenylbenzene

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Hexaphenylbenzene
Structural formula of hexaphenylbenzene.svg
Hexaphenylbenzene xtal.png
Names
Preferred IUPAC name
23,24,25,26-Tetraphenyl-11,21:22,31-terphenyl
Other names
Hexaphenylbenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.356 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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/h1-30H Yes check.svgY
    Key: QBHWPVJPWQGYDS-UHFFFAOYSA-N Yes check.svgY
  • 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/h1-30H
    Key: QBHWPVJPWQGYDS-UHFFFAOYAG
  • c1cc(ccc1)c3c(c(c(c(c3c2ccccc2)c4ccccc4)c5ccccc5)c6ccccc6)c7ccccc7
Properties
C42H30
Molar mass 534.702 g·mol−1
Appearancewhite 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Hexaphenylbenzene is an aromatic compound composed of a benzene ring substituted with six 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]

Contents

Preparation

It is prepared by heating tetraphenylcyclopentadienone and diphenylacetylene in benzophenone or other high-temperature solvent. The reaction proceeds via a Diels–Alder reaction to give the hexaphenyldienone, which then eliminates carbon monoxide. [1]

HexaphenylbenzeneCheletropic.png

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]

Diphenylacetylene cyclotrimerization.png

Structure

Perspective view of the crystal structure of hexaphenylbenzene, showing the rotation of the phenyl rings. Hydrogen atoms have been omitted for clarity. Hexaphenylbenzene xtal perspective.png
Perspective view of the crystal structure of hexaphenylbenzene, showing the rotation of the phenyl rings. Hydrogen atoms have been omitted for clarity.

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

  1. 1 2 Louis Fieser (1966). "Hexaphenylbenzene". Organic Syntheses. 46: 44. doi:10.15227/orgsyn.046.0044.
  2. 1 2 Varun Vij, Vandana Bhalla, and Manoj Kumar (2016). "Hexaarylbenzene: Evolution of Properties and Applications of Multitalented Scaffold". Chemical Reviews. 116 (16): 9565–9627. doi:10.1021/acs.chemrev.6b00144. PMID   27498592.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ↑ W. Herwig, W. Metlesics, H. Zeiss (1959). "π-Complexes of the Transition Metals. X. Acetylenic π-Complexes of Chromium in Organic Synthesis". J. Am. Chem. Soc. 81 (23): 6203–6207. doi:10.1021/ja01532a024.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. 1 2 Bart, J. C. J. (1968). "The crystal structure of a modification of hexaphenylbenzene" (PDF). Acta Crystallographica Section B. 24 (10): 1277–1287. Bibcode:1968AcCrB..24.1277B. doi:10.1107/S0567740868004176.[ permanent dead link ]
  5. ↑ Gust, D. (1977). "Restricted Rotation in Hexaarylbenzenes". J. Am. Chem. Soc. 99 (21): 6980–6982. doi:10.1021/ja00463a034.
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