Hexaphenylethane

Hexaphenylethane is a hypothetical organic compound consisting of an ethane core with six phenyl substituents. All attempts at its synthesis have been unsuccessful.[1] The trityl free radical, Ph3C · , was originally thought to dimerize to form hexaphenylethane. However, an inspection of the NMR spectrum of this dimer reveals that it is in fact a non-symmetrical species, Gomberg's dimer instead.

Hexaphenylethane
Names
Preferred IUPAC name
1,1′,1′′,1′′′,1′′′ ′,1′′′ ′′,1′′′ ′′′-Ethanehexaylhexabenzene
Other names
1,1,1,2,2,2-Hexaphenylethane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C38H30/c1-7-19-31(20-8-1)37(32-21-9-2-10-22-32,33-23-11-3-12-24-33)38(34-25-13-4-14-26-34,35-27-15-5-16-28-35)36-29-17-6-18-30-36/h1-30H
    Key: IPOBVSHPVYWJQC-UHFFFAOYSA-N
  • c1ccc(cc1)C(c2ccccc2)(c3ccccc3)C(c4ccccc4)(c5ccccc5)c6ccccc6
Properties
C38H30
Molar mass 486.658 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

A substituted derivative of hexaphenylethane, hexakis(3,5-di-t-butylphenyl)ethane, has however been prepared. It features a very long central C–C bond at 167 pm (compared to the typical bond length of 154 pm). Attractive London dispersion forces between the t-butyl substituents are believed to be responsible for the stability of this very hindered molecule.[2]

See also

References
  1. Lewars, Errol G. (2008). "Chapter 8: Hexaphenylethane". Modeling Marvels. Springer. pp. 115–129. ISBN 9781402069734.
  2. Rösel, Sören; Balestrieri, Ciro; Schreiner, Peter R. (2017). "Sizing the role of London dispersion in the dissociation of all-meta tert-butyl hexaphenylethane". Chemical Science. 8 (1): 405–410. doi:10.1039/C6SC02727J. ISSN 2041-6520. PMC 5365070. PMID 28451185.

Literature


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