Nitroso

Nitroso compounds are a class of organic chemical compounds having the general structural formula R1R2R3C -N = O. A common feature of all nitroso compounds is the nitroso -N = O functional group.

Nitroso compounds are only stable if no hydrogen is bound to the carbon bearing the functional N-O group, that is none of the radicals R1 to R3 is H ( hydrogen). Otherwise, they rearrange to the tautomeric oximes.

Compounds having a NO group on a carbon (C -nitroso compounds ), and those in which this group is bound to a nitrogen atom (N -nitroso compounds ), such as nitrosamines, nitrosamide and nitrosoureas, differing in their chemical and toxicological properties significantly.

C -nitroso compounds can be aliphatic in, for example, 2 -methyl-2 -nitroso -propane, and aromatic nitro compounds such as nitrosobenzene, differ.

Representation

Aromatic nitroso compounds can be obtained by mild reduction of nitro compounds. Electron-rich aromatics can be nitrosylate under mild conditions with sodium nitrite in acetic acid in an electrophilic substitution reaction. The reactive agent is the NO - cation.

Aliphatic nitroso compounds are formed in the addition of nitrosyl halides such as nitrosyl chloride to alkenes.

Secondary amines react with nitrous acid by replacement of the amino hydrogen to a nitroso formation of water to the corresponding amide, which was then one of the nitramines.

Properties and Uses

Nitroso compounds are in solution and in substance with dimeric structures in equilibrium. They can serve as a "spin trap" for the detection of free radicals.

Proof

Qualitative detection of nitroso compounds is performed with the Tollensprobe. By reaction with zinc dust and ammonium chloride in ethanol, the nitroso compounds are reduced to give hydroxylamine. This reacts with Tollens reagent to elemental silver.