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The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one less carbon atom. [1] [2] [3] The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate.
Amide reduction is a reaction in organic synthesis where an amide is reduced to either an amine or an aldehyde functional group. [1] [2]
Another common example is the reaction of a primary amine or secondary amine with a carboxylic acid or with a carboxylic acid derivative to form an amide. This reaction is widely used, especially in the synthesis of peptides. On the simple addition of an amine to a carboxylic acid, a salt of the organic acid and base is obtained.
Compared to amines, amides are very weak bases. While the conjugate acid of an amine has a pK a of about 9.5, the conjugate acid of an amide has a pK a around −0.5. Therefore, compared to amines, amides do not have acid–base properties that are as noticeable in water. This relative lack of basicity is explained by the withdrawing of ...
Schiff bases are common enzymatic intermediates where an amine, such as the terminal group of a lysine residue, reversibly reacts with an aldehyde or ketone of a cofactor or substrate. The common enzyme cofactor pyridoxal phosphate (PLP) forms a Schiff base with a lysine residue and is transaldiminated to the substrate(s). [ 7 ]
In organic chemistry, the Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually an aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen.
Ammonolysis reactions can be conducted with organic compounds to produce amines (molecules containing a nitrogen atom with a lone pair, :N), [2] or with inorganic compounds to produce nitrides. [3] [4] This reaction is analogous to hydrolysis in which water molecules are split.
Transamidation is a chemical reaction in which an amide reacts with an amine to generate a new amide: RC(O)NR' 2 + HNR" 2 → RC(O)NR" 2 + HNR' 2. The reaction is typically very slow, but it can be accelerated with Lewis acid [1] and organometallic catalysts. [2] Primary amides (RC(O)NH 2) are more amenable to this reaction.