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<p>[QUOTE=&quot;Coinchemistry 2012, post: 2094676, member: 28107&quot;][USER=33176]@Kentucky[/USER]&nbsp; and&nbsp; [USER=17261]@BadThad[/USER]</p><p><br /></p><p>The post I responded to said that fluorocarbons are inert (i.e. completely chemically inactive).&nbsp; When I made those comments, I was referring to potential side reactions with the air and the immediate environment and not necessarily the coinage metals themselves.&nbsp; We were always taught that the halogens were excellent leaving groups and that alkyl halides were generally reactive in substitution and elimination reactions.&nbsp; Now I concede that fluorine is a much poorer leaving group than Cl, Br, or I, but it is my understanding that it can still undergo these reactions.&nbsp; There is a difference in saying that fluorocarbons are less likely to engage in these reactions than other alkyl halides than to suggest that it never happens at all.&nbsp;&nbsp; Here is an example from the Journal of Organic Chemistry demonstrating an intramolecular SN2 reaction with fluorine as a leaving group:&nbsp; <a href="http://pubs.acs.org/doi/abs/10.1021/jo802819p" target="_blank" class="externalLink ProxyLink" data-proxy-href="http://pubs.acs.org/doi/abs/10.1021/jo802819p" rel="nofollow">http://pubs.acs.org/doi/abs/10.1021/jo802819p</a>.&nbsp; Here is another:&nbsp; <a href="http://onlinelibrary.wiley.com/doi/10.1002/ange.201105138/abstract;jsessionid=A9FBD7322D18919C8643D7D9467B35A5.f02t01?deniedAccessCustomisedMessage=&amp;userIsAuthenticated=false" target="_blank" class="externalLink ProxyLink" data-proxy-href="http://onlinelibrary.wiley.com/doi/10.1002/ange.201105138/abstract;jsessionid=A9FBD7322D18919C8643D7D9467B35A5.f02t01?deniedAccessCustomisedMessage=&amp;userIsAuthenticated=false" rel="nofollow">http://onlinelibrary.wiley.com/doi/10.1002/ange.201105138/abstract;jsessionid=A9FBD7322D18919C8643D7D9467B35A5.f02t01?deniedAccessCustomisedMessage=&amp;userIsAuthenticated=false</a>.&nbsp; (And I show these only to suggest that fluorine can serve as a leaving group as the other halogens, not to imply anything more).&nbsp; My point is and was that I wouldn’t rule out the possibility of a reaction and thus wouldn’t consider them inert.</p><p><br /></p><p>And it is also my understanding (and I would love your opinions as it is something I have contemplated in other scenarios such as the use of canned air with alkyl halide propellants and any potential reaction should any propellant land on a coin’s surface), but fluorinated organic compounds make excellent electrophiles and thus are used in inorganic chemistry through oxidative-addition and elimination reactions.&nbsp; Now I understand that this often happens with coordination compounds, but nickel and fluoride compounds are exist.&nbsp; Isn’t it plausible that reactions with the surface of a coin containing nickel or platinum (for instance) could occur using similar chemistry to these reactions?:</p><p><br /></p><p><a href="http://pac.iupac.org/publications/pac/pdf/1972/pdf/3003x0551.pdf" target="_blank" class="externalLink ProxyLink" data-proxy-href="http://pac.iupac.org/publications/pac/pdf/1972/pdf/3003x0551.pdf" rel="nofollow">http://pac.iupac.org/publications/pac/pdf/1972/pdf/3003x0551.pdf</a>.</p><p><br /></p><p>And I want to apologize to [USER=33176]@Kentucky[/USER] if my original post (in terms of tone) might have come off the wrong way.&nbsp; I truly hope this discussion can turn into something educational.[/QUOTE]</p><p><br /></p>

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