Hexaphenylethane: Difference between revisions
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#REDIRECT [[triphenylmethyl radical]] |
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| ImageFile = Hexaphenylethane.svg |
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| ImageSize = 200px |
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| PIN = 1,1′,1′′,1′′′,1′′′ ′,1′′′ ′′,1′′′ ′′′-Ethanehexaylhexabenzene |
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| OtherNames = 1,1,1,2,2,2-Hexaphenylethane |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 17854-07-8 |
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| PubChem = 519482 |
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| ChemSpiderID = 453126 |
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| SMILES = c1ccc(cc1)C(c2ccccc2)(c3ccccc3)C(c4ccccc4)(c5ccccc5)c6ccccc6 |
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| 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 |
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| StdInChIKey = IPOBVSHPVYWJQC-UHFFFAOYSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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| C=38|H=30 |
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| Appearance = |
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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]] [[substituent]]s. All attempts at its [[organic synthesis|synthesis]] have been unsuccessful.<ref>{{cite book | title = Modeling Marvels | pages = 115–129 | date = 2008 | chapter = Chapter 8: Hexaphenylethane | first = Errol G. | last = Lewars | publisher = Springer | isbn = 9781402069734}}</ref> The [[Triphenylmethyl radical|trityl free radical]], Ph<sub>3</sub>C{{middot}}, was originally thought to [[dimer (chemistry)|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. |
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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 force]]s between the [[tert-Butyl|''t''-butyl]] substituents are believed to [[Dispersion stabilized molecules|be responsible for the stability]] of this very hindered molecule.<ref>{{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}}</ref> |
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== See also == |
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* [[Tetraphenylmethane]] |
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==References== |
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{{reflist}} |
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== Literature == |
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* {{cite journal |
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|first1=Yasuto |last1=Uchimura |first2=Takashi |last2=Takeda |first3=Ryo |last3=Katoono |first4=Kenshu |last4=Fujiwara |first5=Takanori |last5=Suzuki | year = 2015 |
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| title = Inside Back Cover: New Insights into the Hexaphenylethane Riddle: Formation of an α,''o''-Dimer |
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| journal = Angewandte Chemie International Edition |
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| volume = 54 |
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| issue = 13 |
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| pages = 4125 |
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| doi = 10.1002/anie.201501649 |
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| pmid = |
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|doi-access=free }} |
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[[Category:Hypothetical chemical compounds]] |
[[Category:Hypothetical chemical compounds]] |
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[[Category:Aromatic hydrocarbons]] |
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{{theoretical-chem-stub}} |
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Latest revision as of 22:59, 23 September 2023
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| Names | |
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| Preferred IUPAC name
1,1′,1′′,1′′′,1′′′ ′,1′′′ ′′,1′′′ ′′′-Ethanehexaylhexabenzene | |
| Other names
1,1,1,2,2,2-Hexaphenylethane
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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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.[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.
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
[edit]References
[edit]- ^ Lewars, Errol G. (2008). "Chapter 8: Hexaphenylethane". Modeling Marvels. Springer. pp. 115–129. ISBN 9781402069734.
- ^ 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
[edit]- 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.
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