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Cyclooctane

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Chemical compound
Cyclooctane
Skeletal formula
Names
Preferred IUPAC name Cyclooctane
Other names Cyclo-octane
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.484 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2Key: WJTCGQSWYFHTAC-UHFFFAOYSA-N
  • InChI=1/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2Key: WJTCGQSWYFHTAC-UHFFFAOYAO
SMILES
  • C1CCCCCCC1
Properties
Chemical formula C8H16
Molar mass 112.216 g·mol
Density 0.840 g/cm
Melting point 14.5 °C (58.1 °F; 287.6 K)
Boiling point 151.2 °C (304.2 °F; 424.3 K)
Solubility in water 7.90 mg/L
Magnetic susceptibility (χ) −91.4·10 cm/mol
Related compounds
Related cycloalkanes Cycloheptane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Cyclooctane is a cycloalkane with the molecular formula (CH2)8. It is a simple colourless hydrocarbon, but it is often a reference compound for saturated eight-membered ring compounds in general.

Cyclooctane has a camphoraceous odor.

Conformations

Further information: Macrocyclic stereocontrol § Cyclooctane

The conformation of cyclooctane has been studied extensively using computational methods. Hendrickson noted that "cyclooctane is unquestionably the conformationally most complex cycloalkane owing to the existence of many conformers of comparable energy". The boat-chair conformation (below) is the most stable form. This conformation was confirmed by Allinger and co-workers. The crown conformation (below) is slightly less stable. Among the many compounds exhibiting the crown conformation (structure II) is S8, elemental sulfur.

Boat-chair Crown
Tub Boat-boat Twist boat-chair Twist chair-chair

Synthesis and reactions

The main route to cyclooctane derivatives involves the dimerization of butadiene, catalysed by nickel(0) complexes such as nickel bis(cyclooctadiene). This process affords, among other products, 1,5-cyclooctadiene (COD), which can be hydrogenated. COD is widely used for the preparation of precatalysts for homogeneous catalysis. The activation of these catalysts under H2, produces cyclooctane, which is usually discarded or burnt:

C8H12 + 2 H2 → C8H16

Cyclooctane participates in no reactions except those typical of other saturated hydrocarbons, combustion and free radical halogenation. Work in 2009 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.

Amination of cyclooctane by nitrobenzene

References

  1. ^ ECHA REACH
  2. Mackay, Donald (2006). Handbook of Physical-chemical Properties and Environmental Fate for Organic Chemicals. CRC Press. p. 258. ISBN 978-1-56670-687-2.
  3. Sell, C. S. (2006). "On the Unpredictability of Odor". Angew. Chem. Int. Ed. 45 (38): 6254–6261. doi:10.1002/anie.200600782. PMID 16983730.
  4. 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:10.1021/ja01002a036.
  5. 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:10.1021/j100248a015.
  6. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "crown conformation". doi:10.1351/goldbook.C01422
  7. ^ Pakes, P. W.; Rounds, T. C.; Strauss, H. L. (1981). "Conformations of cyclooctane and some related oxocanes". The Journal of Physical Chemistry. 85 (17): 2469–2475. doi:10.1021/j150617a013. ISSN 0022-3654.
  8. Moss, G. P. (1996). "Basic terminology of stereochemistry (IUPAC Recommendations 1996)". Pure and Applied Chemistry. 68 (12): 2193–2222. doi:10.1351/pac199668122193. ISSN 0033-4545. S2CID 98272391.
  9. Thomas Schiffer, Georg Oenbrink, “Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene” in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_205.
  10. Deng, Guojun; Wenwen Chen; Chao-Jun Li (February 2009). "An Unusual Peroxide-Mediated Amination of Cycloalkanes with Nitroarenes". Advanced Synthesis & Catalysis. 351 (3): 353–356. doi:10.1002/adsc.200800689.
Cycloalkanes
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