hexaphenylethane
{{Chembox
| ImageFile = Hexaphenylethane.svg
| ImageSize = 200px
| PIN = 1,1′,1′′,1′′′,1′′′ ′,1′′′ ′′,1′′′ ′′′-Ethanehexaylhexabenzene
| OtherNames = 1,1,1,2,2,2-Hexaphenylethane
| Section1 = {{Chembox Identifiers
| CASNo = 17854-07-8
| PubChem = 519482
| ChemSpiderID = 453126
| SMILES = c1ccc(cc1)C(c2ccccc2)(c3ccccc3)C(c4ccccc4)(c5ccccc5)c6ccccc6
| StdInChI=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
| StdInChIKey = IPOBVSHPVYWJQC-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=38|H=30
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| Section3 = {{Chembox Hazards
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Hexaphenylethane is a hypothetical organic compound consisting of an ethane core with six phenyl substituents. All attempts at its synthesis have been unsuccessful.{{cite book | title = Modeling Marvels | pages = 115–129 | date = 2008 | chapter = Chapter 8: Hexaphenylethane | first = Errol G. | last = Lewars | publisher = Springer | isbn = 9781402069734}} The trityl free radical, Ph3C{{middot}}, 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.{{Cite journal|last1=Rösel|first1=Sören|last2=Balestrieri|first2=Ciro|last3=Schreiner|first3=Peter R.|date=2017|title=Sizing the role of London dispersion in the dissociation of all-meta tert-butyl hexaphenylethane|url= |journal=Chemical Science|language=en|volume=8|issue=1|pages=405–410|doi=10.1039/C6SC02727J|issn=2041-6520|pmc=5365070|pmid=28451185}}
See also
References
{{reflist}}
Literature
- {{cite journal
|first1=Yasuto |last1=Uchimura |first2=Takashi |last2=Takeda |first3=Ryo |last3=Katoono |first4=Kenshu |last4=Fujiwara |first5=Takanori |last5=Suzuki | year = 2015
| title = Inside Back Cover: New Insights into the Hexaphenylethane Riddle: Formation of an α,o-Dimer
| journal = Angewandte Chemie International Edition
| volume = 54
| issue = 13
| pages = 4125
| doi = 10.1002/anie.201501649
| pmid =
|doi-access=free }}
Category:Hypothetical chemical compounds
Category:Aromatic hydrocarbons
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