Trifluoronitrosomethane Explained

Trifluoronitrosomethane (commonly abbreviated TFNM) is a toxic organic compound consisting of a trifluoromethyl group covalently bound to a nitroso group. Its distinctive deep blue color is unusual for a gas.

History

Trifluoronitrosomethane was synthesized for the first time in 1936 by Otto Ruff and Manfred Giese at the Schlesische Friedrich-Wilhelms-Universität zu Breslau.^[1] It was created through 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% in normal pressure. A small amount of mercury is needed as catalyst. The reaction results in the creation of iodine as a by-product.^{[2] [3] [4]}

Properties

Although it is somewhat more kinetically stable due to its fluorine substituents, trifluoronitrosomethane, like other nitroso compounds, has a weak C–N bond of only 39.9 kcal/mol.^[5]

Related

Trifluoronitrosoethylene is also a similar deep blue gas.^[6]

See also

• Trichloronitrosomethane

Notes and References

1. Otto Ruff . Otto . Ruff . Manfred . Giese . Das Trifluor-nitroso-methan, CF₃.NO (III.) . Ber Dtsch Chem Ges . 69 . 1936 . 4 . 684–689 . 10.1002/cber.19360690411.
2. Alexander . Senning . N-, 0-, and S-trihalomethyl compounds . . 65 . 1964 . 4 . 385–412 . 10.1021/cr60236a001 .
3. C. W. . Taylor . T. J. . Brice . R. L. . Wear . The Preparation of Polyfluoronitrosoalkanes from Nitrosyl Polyfluoroacylates . Journal of Organic Chemistry . 27 . 1962 . 3 . 1064–1066 . 10.1021/jo01050a523.
4. J. D. . Park . R. W. . Rosser . J. R. . Lacher . Preparation of Perfluoronitrosoalkanes. Reaction of Trifluoroacetic Anhydride with Nitrosyl Chloride . Journal of Organic Chemistry . 27 . 1962 . 4 . 1642 . 10.1021/jo01051a519.
5. Book: Luo, Yu-Ran. Comprehensive Handbook of Chemical Bond Energies. CRC Press. 2007. 978-0-8493-7366-4. Boca Raton, Fl.. 406.
6. Griffin . C. E. . Haszeldine . R. N. . 279. Perfluoroalkyl derivatives of nitrogen. Part VIII. Trifluoronitrosoethylene and its polymers . Journal of the Chemical Society (Resumed) . 1960 . 1398–1406 . 10.1039/JR9600001398.