Trifluoronitrosomethane

Trifluoronitrosomethane is a toxic and unstable gaseous compound consisting of a trifluoromethyl group covalently bound to a nitroso group. The gas is notable for its dark blue colour.

History

Trifluoronitrosomethane was synthesised for the first time in 1936 by Otto Ruff and Manfred Giese at the Schlesische Friedrich-Wilhelms-Universität zu Breslau. It was formed through a reaction involving the fluorination of silver cyanide in the presence of silver nitrate and silver oxide.

Production

Trifluoronitrosomethane can be produced from the reaction of trifluoroiodomethane and nitric oxide under a UV light with a yield of up to 90%. A significant amount of mercury metal is needed to quench the iodine and nitrogen dioxide gases produced during the reaction.
Pyrolysis of trifluoroacetyl nitrite gives trifluoronitrosomethane with yields over 85%. Carbon dioxide is formed as a side product. This method may also be employed to make other perfluoronitrosoalkanes from the corresponding perfluorocarboxylic acids.

Properties

Although it is somewhat more kinetically stable than expected due to its fluorine substituents, trifluoronitrosomethane, like other nitroso compounds, has a C–N bond that is weaker than normal. The bond enthalpy of the C–N bond is only 167 kJ/mol.