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Hexaphenylethane

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, Ph3· , 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.

Hexaphenylethane
Names
Preferred IUPAC name
1,1′,1′′,1′′′,1′′′ ′,1′′′ ′′,1′′′ ′′′-Ethanehexaylhexabenzene
Other names
1,1,1,2,2,2-Hexaphenylethane
Identifiers
  • 17854-07-8
3D model (JSmol)
  • Interactive image
ChemSpider
  • 453126
  • 519482
  • DTXSID10894912
  • 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).

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

  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.

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.


hexaphenylethane, hypothetical, organic, compound, consisting, ethane, core, with, phenyl, substituents, attempts, synthesis, have, been, unsuccessful, trityl, free, radical, ph3c, originally, thought, dimerize, form, hexaphenylethane, however, inspection, spe. 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 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 DTXSID10894912 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 30HKey IPOBVSHPVYWJQC UHFFFAOYSA N SMILES c1ccc cc1 C c2ccccc2 c3ccccc3 C c4ccccc4 c5ccccc5 c6ccccc6 Properties Chemical formula C 38H 30 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 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 editTetraphenylmethaneReferences edit Lewars Errol G 2008 Chapter 8 Hexaphenylethane Modeling Marvels Springer pp 115 129 ISBN 9781402069734 Rosel Soren 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 editUchimura Yasuto Takeda Takashi Katoono Ryo Fujiwara Kenshu Suzuki Takanori 2015 Inside Back Cover New Insights into the Hexaphenylethane Riddle Formation of an a o Dimer Angewandte Chemie International Edition 54 13 4125 doi 10 1002 anie 201501649 nbsp This article about theoretical chemistry is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Hexaphenylethane amp oldid 1176777161, wikipedia, wiki, book, books, library,

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