Norbornane
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Surname | Norbornane | ||||||||||||||||||
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Molecular formula | C 7 H 12 | ||||||||||||||||||
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Molar mass | 96.17 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
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Melting point |
85-88 ° C |
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Norbornane (systematically: bicyclo [2.2.1] heptane ) is an organic compound , a saturated hydrocarbon with the empirical formula C 7 H 12 . At room temperature it is a crystalline solid. Structurally, it is a cyclohexane ring with a methylene bridge .
properties
An interesting property of this compound is its ability to form norbornyl carbonium ions - five-bonded carbocations of alkanes - by taking up a proton with a superacid . Since the 1950s there had been a decade-long dispute between Saul Winstein (non-classical character) and his critic Herbert C. Brown about the non-classical character of the 2-norbornyl cation , until the non-classical character was finally proven experimentally.
Related bicyclic compounds are norbornene , which has the same carbon structure but one double bond , and norbornadiene , also with the same structure but two double bonds and thus a diene .
use
Some norbornane derivatives are used as intermediates in the pharmaceutical industry, e.g. B. Camphor oxime .
See also
The synthesis of a saturated C 11 H 16 hydrocarbon called trinorbornane , which contains three norbornane structural elements, was published in 2017.
Individual evidence
- ↑ a b c d data sheet norbornane from Sigma-Aldrich , accessed on June 14, 2011 ( PDF ).
- ↑ Observation of 2-norbornyl carbonium
- ↑ Mark Peplow: The nonclassical cation: a classic case of conflict Chemistry World, July, 20, 2013.
- ↑ Lorenzo Delarue Bizzini, Thomas Müntener, Daniel Häussinger, Markus Neuburger, Marcel Mayor: Synthesis of trinorbornane . In: Chem. Commun. tape 53 , no. 83 , 2017, p. 11399 , doi : 10.1039 / c7cc06273g ( unibas.ch [PDF]).