Introduction to Reaction of Amines with Nitrous Acid
Nitrous acid (HNO2 or HONO) reacts with aliphatic amines in a way which offers a helpful test for differentiate primary, secondary and tertiary amines.
1°-Amines + HONO (cold acidic solution) -------> Nitrogen Gas Evolution from a Clear Solution
2°-Amines + HONO (cold acidic solution) -------->An Insoluble Oil (N-Nitrosamine)
3°-Amines + HONO (cold acidic solution) -------->A Clear Solution (Ammonium Salt Formation)
Nitrous acid is a Brønsted acid of moderate strength (pKa = 3.3). since it is unstable, it is prepared immediately before make use of in the following manner:
Under the acidic conditions of this reaction, all amines go through reversible salt formation:
This occurs with 3º-amines, and the salts are generally soluble in water. The reactions of nitrous acid with 1°- and 2°- aliphatic amines might be described by considering their behavior with the nitrosonium cation, NO(+), an electrophilic species exist in acidic nitrous acid solutions.
The different behavior of 1º, 2º & 3º-aliphatic amines is an instructive challenge to our understanding of their chemistry, but is of little significance as a synthetic tool. The SN1 result mixtures from 1º-amines are hard to control, and rearrangement is familiar when branched primary alkyl groups are concerned. The N-nitrosamines formed from 2º-amines are carcinogenic, and are not normally helpful as intermediates for subsequent reactions.
Nitrous acid reactions of 1º-aryl amines generate comparatively stable diazonium species that serve as intermediates for a range of aromatic substitution reactions. Diazonium cations might be explained by resonance contributors, like in the bracketed formulas displayed below in the diagram. The left-hand contributor is dominant since it has greater bonding. The Loss of nitrogen is slower than in aliphatic 1º-amines since the C-N bond is stronger, and aryl carbocations are relatively unstable.
Aqueous solutions of these diazonium ions have enough stability at 0º to 10 ºC that they may be employed as intermediates in a range of nucleophilic substitution reactions. For an instance, if water is the only nucleophile presented for reaction, phenols are formed in the good yield.
2º-Aryl amines provide N-nitrosamine derivatives on reaction with nitrous acid, and So behave identically to their aliphatic counterparts.
Depending on ring substitution, 3º-Aryl amines may go through aromatic ring nitrosation at sites ortho or para to the amine substituent. The nitrosonium cation is not adequately electrophilic to react with benzene itself or even toluene, but the highly activated aromatic rings like phenols and amines are capable of substitution. Obviously, the rate of reaction of NO(+) directly at nitrogen is greater than that of ring substitution, as displayed in the preceding example. Once nitrosated, the activating character of the amine nitrogen is very much diminished; and N-nitrosoaniline derivatives, or certainly any amide derivatives, do not go through ring nitrosation.
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