Amination is the process by which an amine group is introduced into an organic molecule. This type of reaction is important because organonitrogen compounds are pervasive.
Reactions[edit]
Aminase enzymes[edit]
Enzymes that catalyse this reaction are termed aminases. Amination can occur in a number of ways including reaction with ammonia or another amine such as an alkylation, reductive amination and the Mannich reaction.
Acid-catalysed hydroamination[edit]
Many alkyl amines are produced industrially by the amination of alcohols using ammonia in the presence of solid acid catalysts. Illustrative is the production of tert-butylamine:
- NH3 + CH2=C(CH3)2 → H2NC(CH3)3
The Ritter reaction of isobutene with hydrogen cyanide is not useful in this case because it produces too much waste.[1]
Electrophilic amination[edit]
Usually, the amine reacts as the nucleophile with another organic compound acting as the electrophile. This sense of reactivity may be reversed for some electron-deficient amines, including oxaziridines, hydroxylamines, oximes, and other N–O substrates. When the amine is used as an electrophile, the reaction is called electrophilic amination. Electron-rich organic substrates that may be used as nucleophiles for this process include carbanions and enolates.
Miscellaneous methods[edit]
Alpha hydroxy acids can be converted into amino acids directly using aqueous ammonia solution, hydrogen gas and a heterogeneous metallic ruthenium catalyst.[2]
Metal-catalyzed hydroamination[edit]
In hydroamination, amines add to alkenes.[3]
See also[edit]
- Alkylation, the addition of an alkyl group
- Acylation, the addition of an acyl group (-C(O)R)
- Deamination
References[edit]
- ^ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3527306732.
- ^ Deng, Weiping, et al. "Catalytic amino acid production from biomass-derived intermediates." Proceedings of the National Academy of Sciences 115.20 (2018): 5093-5098. doi:10.1073/pnas.1800272115
- ^ Liangbin Huang, Matthias Arndt, Käthe Gooßen, Heinrich Heydt, and Lukas J. Gooßen "Late Transition Metal-Catalyzed Hydroamination and Hydroamidation" Chem. Rev., 2015, 115 (7), pp 2596–2697. doi:10.1021/cr300389u