| Cyclooctane | |
|---|---|
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| Identifiers | |
| CAS number | 292-64-8  |
| SMILES |
C1CCCCCCC1
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| Properties | |
| Molecular formula | C8H16 |
| Molar mass | 112.21 g/mol |
| Density | 0.834 g/cm3 |
| Melting point |
14.59 °C |
| Boiling point |
149 °C |
| Solubility in water | 7.90 mg/L |
| Related compounds | |
| Related cycloalkanes | Cycloheptane |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Cyclooctane is a cycloalkane with the molecular formula C8H16.[1]
Cyclooctane is representative of eight-membered ring compounds in general, and its conformation has therefore been studied extensively using computational methods. Hendrickson noted that "cyclooctane is unquestionably the conformationally most complex cycloalkane owing to the existence of so many forms of comparable energy", but he deduced that the boat-chair conformation I is the most stable form.[2] This was confirmed by Allinger and co-workers.[3] The crown conformation[4] II is slightly less stable.
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The boat-chair (I) and crown {II) conformations of cyclooctane
Chemistry
As an alkane, cyclooctane has few reactions aside from combustion and free radical halogenation. Recent work on alkane functionalisation, using peroxides such as dicumyl peroxide, has opened up the chemistry to some extent, allowing for example the introduction of a phenylamino group.[5]
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Amination of cyclooctane by nitrobenzene
References
- ^ Mackay, Donald (2006). Handbook of Physical-chemical Properties and Environmental Fate for Organic Chemicals. CRC Press. p. 258. ISBN 1566706874. http://books.google.com/books?id=wjd-nEugVskC.
- ^ Hendrickson, James B. (1967), "Molecular Geometry V. Evaluation of Functions and Conformations of Medium Rings", Journal of the American Chemical Society 89 (26): 7036–7043, doi:
- ^ Dorofeeva, O.V.; Mastryukov, V.S.; Allinger, N.L.; Almenningen, A. (1985). "The molecular structure and conformation of cyclooctane as determined by electron diffraction and molecular mechanics calculations". The Journal of Physical Chemistry 89 (2): 252–257. doi:. http://pubs.acs.org/doi/pdf/10.1021/j100248a015. Retrieved 2008-02-05.
- ^ International Union of Pure and Applied Chemistry. "crown conformation". Compendium of Chemical Terminology Internet edition.
- ^ Deng, Guojun; Wenwen Chen, Chao-Jun Li (February 2009). "An Unusual Peroxide-Mediated Amination of Cycloalkanes with Nitroarenes". Advanced synthesis & catalysis 351: 353–356. doi:.
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