directions of aromatic amines and aliphatic amines with nitrous acid
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Nitrous acid (HNO2HNO2 or HONOHONO) reacts with aliphatic amines in a fashion that provides a useful test for distinguishing primary, secondary and tertiary amines.
1°-Amines + HONO (cold acidic solution) →→Nitrogen Gas Evolution from a Clear Solution2°-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). Because it is unstable, it is prepared immediately before use in the following manner:
Under the acidic conditions of this reaction, all amines undergo reversible salt formation:
This happens with 3º-amines, and the salts are usually soluble in water. The reactions of nitrous acid with 1°- and 2°- aliphatic amines may be explained by considering their behavior with the nitrosonium cation, NO(+), an electrophilic species present in acidic nitrous acid solutions.
1°-Amines + HONO (cold acidic solution) →→Nitrogen Gas Evolution from a Clear Solution2°-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). Because it is unstable, it is prepared immediately before use in the following manner:
Under the acidic conditions of this reaction, all amines undergo reversible salt formation:
This happens with 3º-amines, and the salts are usually soluble in water. The reactions of nitrous acid with 1°- and 2°- aliphatic amines may be explained by considering their behavior with the nitrosonium cation, NO(+), an electrophilic species present in acidic nitrous acid solutions.
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