Hexaphenylethane
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| Surname | Hexaphenylethane | |||||||||
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1,1,1,2,2,2-hexaphenylethane ( IUPAC ) |
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| Molecular formula | C 38 H 30 | |||||||||
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| Molar mass | 486.658 g mol −1 | |||||||||
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
Hexaphenylethane is a hypothetical organic compound that consists of a six-fold phenyl - substituted ethane center . However, so far no synthesis attempt has been successful. Originally it was thought that hexaphenylethane could be obtained by dimerizing the free trityl radical . However, NMR spectroscopic experiments showed that the asymmetrical Gombergs dimer is formed in reality . A main reason against symmetrical dimerization is too high a steric demand on the phenyl groups .
However, it was possible to synthesize a substituted derivative, hexakis (3,5- di - t -butylphenyl) ethane. This is characterized by a very large C – C distance between the central carbon atoms of 167 pm compared to typical single bonds (154 pm). It is believed that London dispersion interactions between the tert -butyl substituents make central contributions to the stability of this sterically hindered molecule.
See also
- Tetraphenylmethane
- Hexaphenyldisilane (synthesizable organosilicon analogue)
Individual evidence
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ Errol G. Lewars: Chapter 8: Hexaphenylethane . In: Modeling Marvels 2008, ISBN 9781402069734 , pp. 115-129.
- ↑ Sören Rösel, Ciro Balestrieri, Peter R. Schreiner: Sizing the role of London dispersion in the dissociation of general- meta tert -butyl hexaphenylethane . In: Chemical Science . 8, No. 1, 2017, ISSN 2041-6520 , pp. 405-410. doi : 10.1039 / C6SC02727J . PMC 5365070 (free full text).
literature
- Yasuto Uchimura, Takashi Takeda, Ryo Katoono, Kenshu Fujiwara, Takanori Suzuki: Inside Back Cover: New Insights into the Hexaphenylethane Riddle: Formation of an α, o -Dimer . In: Angewandte Chemie International Edition . 54, No. 13, 2015, p. 4125. doi : 10.1002 / anie.201501649 .