The Organic Chemist's Book of Orbitals by William L. Jorgensen

By William L. Jorgensen

Publication via William L. Jorgensen, Lionel Salem

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Bistrifluoromethyl mercury is a white crystalline solid which dissolves in water, from which it may be recovered. , [ H g ( C F 3 ) 4 ] ^ " and [ H g ( C F 3 ) 2 0 H ] - ) rather than C F 3 - ions. In contrast, dimethylmercury is a covalent liquid without any trace of ionic character. This behavior suggests that C F 3 in this context behaves more as a pseudohalogen and that the bisperfluoroalkyl compound is more akin to a mercuric halide. This view is strongly supported by the results o f conductometric titrations.

It is found, for example, that sodium hydride reacts with boron trifluoride at - 7 0 ° to give N a ( B F 3 H ) . There are also various alkoxy trifluoroborates, as well as derivatives with the anions [ B F 3 ( O H ) ] - and [ B F 3 0 ] ^ - . D i - and mono-fluoroborates are less stable than trifluoroborates. A few salts o f H [ B F 2 ( O H ) 2 ] have been iso­ lated and mention may also be made o f phenyl-substituted fluoroborates such as those containing the [ B F ( P h ) 3 ] - anion. Y e t another interesting type o f anionic species is that con­ taining two halogens, such as [BF3C1]~.

Deriva­ tives o f the [B2Cl6]^~ ion have been prepared in precisely this way. The Carbon Fluorides The carbon fluorides occupy a special position among derivatives o f the non-metals both because o f their number and because o f their unique properties. Carbon-fluorine com­ pounds are known which match most o f the main types o f carbon-hydrogen compounds. This is not surprising since the fluorine atom is small and it also forms a bond with carbon which is strong ( C — F , ca, 107 kcal/mole; C — H , ca.

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