Editing Fluorocarbon (section)

===Chemical properties===
Perfluoroalkanes are very stable because of the strength of the [[carbon–fluorine bond]], one of the strongest in organic chemistry.<ref name=hagan>
{{cite journal
 |author=O'Hagan D
 |title=Understanding organofluorichemistry. An introduction to the C–F bond
 |journal=Chem. Soc. Rev.
 |date=February 2008
 |volume=37
 |issue=2
 |pages=308–19
 |pmid=18197347
 |doi=10.1039/b711844a
}}
</ref>
Its strength is a result of the electronegativity of fluorine imparting partial ionic character through [[partial charge]]s on the carbon and fluorine atoms, which shorten and strengthen the bond (compared to carbon-hydrogen bonds) through favorable [[covalent]] interactions. Additionally, multiple carbon–fluorine bonds increase the strength and stability of other nearby carbon–fluorine bonds on the same [[geminal]] carbon, as the carbon has a higher positive partial charge.<ref name=Lemal/> Furthermore, multiple carbon–fluorine bonds also strengthen the "skeletal" carbon–carbon bonds from the [[inductive effect]].<ref name=Lemal/> Therefore, [[Saturated and unsaturated compounds|saturated]] fluorocarbons are more chemically and thermally stable than their corresponding hydrocarbon counterparts, and indeed any other organic compound. They are susceptible to attack by very strong reductants, e.g. [[Birch reduction]] and very specialized organometallic complexes.<ref name=kip>
{{cite journal
 |vauthors=Kiplinger JL, Richmond TG, Osterberg CE
 |title=Activation of Carbon-Fluorine Bonds by Metal Complexes
 |journal=Chem. Rev.
 |volume=94
 |issue=2
 |pages=373–431
 |year=1994
 |doi=10.1021/cr00026a005
 }}
</ref>

Fluorocarbons are colorless and have high density, up to over twice that of water. They are not miscible with most organic solvents (e.g., ethanol, acetone, ethyl acetate, and chloroform), but are miscible with some hydrocarbons (e.g., hexane in some cases). They have very low solubility in water, and water has a very low solubility in them (on the order of 10 ppm). They have low [[refractive index|refractive indices]].

{{Image frame|content=<chem>\overset{\delta+}{C}-\overset{\delta-}{F}</chem>|caption=The partial charges in the polarized carbon–fluorine bond|width=150}}

As the high [[electronegativity]] of fluorine reduces the [[polarizability]] of the atom,<ref name=Lemal/> fluorocarbons are only weakly susceptible to the fleeting dipoles that form the basis of the [[London dispersion force]]. As a result, fluorocarbons have low intermolecular attractive forces and are [[lipophobic]] in addition to being [[hydrophobe|hydrophobic]] and [[non-polar]]. Reflecting the weak [[intermolecular force]]s these compounds exhibit low [[viscosity|viscosities]] when compared to liquids of similar [[boiling point]]s, low [[surface tension]] and low [[heat of vaporization|heats of vaporization]]. The low [[attractive force]]s in fluorocarbon liquids make them [[compressible]] (low [[bulk modulus]]) and able to dissolve gas relatively well. Smaller fluorocarbons are extremely [[volatility (chemistry)|volatile]].<ref name=Lemal/> There are five perfluoroalkane gases: [[tetrafluoromethane]] (bp −128&nbsp;°C), [[hexafluoroethane]] (bp −78.2&nbsp;°C), [[octafluoropropane]] (bp −36.5&nbsp;°C), [[perfluorobutane|perfluoro-n-butane]] (bp −2.2&nbsp;°C) and perfluoro-iso-butane (bp −1&nbsp;°C). Nearly all other fluoroalkanes are liquids; the most notable exception is [[perfluorocyclohexane]], which [[sublimation (chemistry)|sublimes]] at 51&nbsp;°C.<ref>{{cite web |url=http://www.ornl.gov/~webworks/cpr/v823/rpt/108771.pdf |title=Archived copy |access-date=2008-11-29 |url-status=dead |archive-url=https://web.archive.org/web/20081205213815/http://www.ornl.gov/~webworks/cpr/v823/rpt/108771.pdf |archive-date=2008-12-05 }}</ref> Fluorocarbons also have low [[surface energy|surface energies]] and high [[dielectric]] strengths.<ref name=Lemal/>

<gallery caption="Perfluoroalkanes" widths="150px" heights="120px" perrow="5">
File:Tetrafluormethan.svg|[[Carbon tetrafluoride]], the simplest perfluoroalkane
File:Perfluorooctane.png|[[Perfluorooctane]], a linear perfluoroalkane
File:Perfluoro(2-methylpentane).svg|[[Perfluoro-2-methylpentane]], a branched perfluoroalkane
File:Perfluoro-1,3-dimethylcyclohexane.svg|[[Perfluoro-1,3-dimethylcyclohexane]], a cyclic perfluoroalkane
File:Perfluorodecaline.svg|[[Perfluorodecalin]], a polycyclic perfluoroalkane
</gallery>