Article · Wikipedia archive · Last revised Jul 16, 2026

Hexaphenylethane

Hexaphenylethane is a hypothetical organic compound consisting of an ethane core with six phenyl substituents. As of 2022, all attempts at its synthesis have been unsuccessful. 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.

Last revised
Jul 16, 2026
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Source
Wikipedia ↗
Hexaphenylethane
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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).

Hexaphenylethane is a hypothetical organic compound consisting of an ethane core with six phenyl substituents. As of 2022, all attempts at its synthesis have been unsuccessful.12 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.

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.3

See also

See also

References

References

  1. Lewars, Errol G. (2008). "Chapter 8: Hexaphenylethane". Modeling Marvels. Springer. pp. 115–129. ISBN 9781402069734.
  2. Rösel, Sören; Schreiner, Peter R. (2022). "Computational Chemistry as a Conceptual Game Changer: Understanding the Role of London Dispersion in Hexaphenylethane Derivatives (Gomberg Systems)". Israel Journal of Chemistry. 62 (1–2). doi:10.1002/ijch.202200002. ISSN 0021-2148. Retrieved 2025-11-22.
  3. 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.

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