Chemistry:Hexaphenylethane
Hexaphenylethane is a hypothetical organic compound consisting of an ethane core with six phenyl substituents. As of 2022[update], all attempts at its synthesis have been unsuccessful.[1][2] 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
References
- ↑ Lewars, Errol G. (2008). "Chapter 8: Hexaphenylethane". Modeling Marvels. Springer. pp. 115–129. ISBN 9781402069734.
- ↑ 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. https://onlinelibrary.wiley.com/doi/10.1002/ijch.202200002. Retrieved 2025-11-22.
- ↑ Rösel, Sören; Balestrieri, Ciro; Schreiner, Peter R. (2017). "Sizing the role of London dispersion in the dissociation of all-meta tert-butyl hexaphenylethane" (in en). Chemical Science 8 (1): 405–410. doi:10.1039/C6SC02727J. ISSN 2041-6520. PMID 28451185.
Literature
- Uchimura, Yasuto; Takeda, Takashi; Katoono, Ryo; Fujiwara, Kenshu; Suzuki, Takanori (2015). "Inside Back Cover: New Insights into the Hexaphenylethane Riddle: Formation of an α,o-Dimer". Angewandte Chemie International Edition 54 (13): 4125. doi:10.1002/anie.201501649.
 |  |
