Hexaphenylethane: Difference between revisions

Hexaphenylethane
Names
	Preferred IUPAC name 1,1′,1′′,1′′′,1′′′ ′,1′′′ ′′,1′′′ ′′′-Ethanehexaylhexabenzene
	Other names 1,1,1,2,2,2-Hexaphenylethane
Identifiers
CAS Number	17854-07-8;
3D model (JSmol)	Interactive image;
ChemSpider	453126;
PubChem CID	519482;
CompTox Dashboard (EPA)	DTXSID201335989 DTXSID10894912, DTXSID201335989 ;
	InChI 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;
	SMILES c1ccc(cc1)C(c2ccccc2)(c3ccccc3)C(c4ccccc4)(c5ccccc5)c6ccccc6;
Properties
Chemical formula	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

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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]

References

^ 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

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.

This article about theoretical chemistry is a stub. You can help Wikipedia by expanding it.

[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.

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[2]

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 | ImageFile = Hexaphenylethane.svg
 | ImageSize = 200px
+| PIN = 1,1′,1′′,1′′′,1′′′&nbsp;′,1′′′&nbsp;′′,1′′′&nbsp;′′′-Ethanehexaylhexabenzene
-| IUPACName = 1,1,1,2,2,2-Hexaphenylethane
-| OtherNames =
+| OtherNames = 1,1,1,2,2,2-Hexaphenylethane
 | Section1 = {{Chembox Identifiers
 | CASNo = 17854-07-8
@@ Line 27: / Line 27: @@
 }}
-'''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 | isbn = 9781402069734}}</ref>  The [[trityl]] [[free radical]], Ph<sub>3</sub>C<sup>•</sup>, was originally thought to [[dimer]]ize to form hexaphenylethane.  However, an inspection of the [[NMR spectrum]] of this dimer reveals that it is in fact a non-symmetrical species rather than hexaphenylethane, due to the severe [[steric hindrance|steric repulsions]] that hexaphenylethane would experience.  However, paradoxically, a substituted derivative of hexaphenylethane, hexakis(3,5-di-''t''-butylphenyl)ethane, has been prepared and features a very long central C–C bond at 167&nbsp;pm (compared to the typical bond length of 154&nbsp;pm).  Attractive [[London dispersion force]]s between the [[tert-Butyl|''t''-butyl]] substituents are believed to be responsible for the stability of this very hindered molecule.<ref>{{Cite journal|last=Rösel|first=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=http://pubs.rsc.org/en/Content/ArticleLanding/2017/SC/C6SC02727J#!divAbstract|journal=Chemical Science|language=en|volume=8|issue=1|pages=405–410|doi=10.1039/C6SC02727J|issn=2041-6520}}</ref>
+'''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.
+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&nbsp;pm (compared to the typical bond length of 154&nbsp;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>
 == See also ==
 * [[Tetraphenylmethane]]
-* [[Triphenylmethyl radical]]
-* [[3-triphenylmethyl-6-diphenylmethylidene-1,4-cyclohexadiene]]
 ==References==
@@ Line 47: / Line 47: @@
 | doi = 10.1002/anie.201501649
 | pmid =
+|doi-access=free }}
-}}
 [[Category:Hypothetical chemical compounds]]
 [[Category:Aromatic hydrocarbons]]
+{{theoretical-chem-stub}}