# Amination

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{{Short description|Chemical reaction}}
{{distinguish|animation}}
'''Amination''' is the process by which an [amine](/source/amine) group is introduced into an organic [molecule](/source/molecule). This type of reaction is important because organonitrogen compounds are pervasive.

==Reactions==
===Aminase enzymes===
Enzymes that [catalyse](/source/catalysis) this reaction are termed '''aminases'''. Amination can occur in a number of ways including reaction with [ammonia](/source/ammonia) or another [amine](/source/amine) such as an [alkylation](/source/alkylation), [reductive amination](/source/reductive_amination) and the [Mannich reaction](/source/Mannich_reaction).

===Acid-catalysed hydroamination===
Many alkyl amines are produced industrially by the amination of alcohols using ammonia in the presence of [solid acid](/source/solid_acid) catalysts, to [dehydrate the alcohol](/source/Dehydration_reaction) into an alkene.  Illustrative is the production of ''tert''-butylamine:
:NH<sub>3</sub>  +  CH<sub>2</sub>=C(CH<sub>3</sub>)<sub>2</sub>  →   H<sub>2</sub>NC(CH<sub>3</sub>)<sub>3</sub>
The [Ritter reaction](/source/Ritter_reaction) of [isobutene](/source/isobutene) with [hydrogen cyanide](/source/hydrogen_cyanide) is not useful in this case because it produces too much waste.<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a02_001|title=Amines, Aliphatic|year=2000|last1= Eller|first1=Karsten|last2=Henkes|first2=Erhard|last3=Rossbacher|first3=Roland|last4=Höke|first4=Hartmut|isbn=3527306730}}</ref>

=== Electrophilic amination ===
{{Main|Electrophilic amination}}
Usually, the amine reacts as the [nucleophile](/source/nucleophile) with another organic compound acting as the [electrophile](/source/electrophile). This sense of reactivity may be reversed for some electron-deficient amines, including [oxaziridine](/source/oxaziridine)s, [hydroxylamine](/source/hydroxylamine)s, [oxime](/source/oxime)s, and other N–O substrates. When the amine is used as an electrophile, the reaction is called [electrophilic amination](/source/electrophilic_amination). Electron-rich organic substrates that may be used as nucleophiles for this process include [carbanion](/source/carbanion)s and [enolate](/source/enolate)s.

===Miscellaneous methods===
[Alpha hydroxy acids](/source/Alpha_hydroxy_acids) can be converted into amino acids directly using aqueous ammonia solution, hydrogen gas and a heterogeneous metallic [ruthenium](/source/ruthenium) catalyst.<ref> 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}}</ref>

===Metal-catalyzed hydroamination===
In [hydroamination](/source/hydroamination), amines add to [alkene](/source/alkene)s.<ref>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}}</ref>  When substituted amines add, the result is [alkene carboamination](/source/alkene_carboamination).

==See also==
*[Alkylation](/source/Alkylation), the addition of an [alkyl](/source/alkyl) group
*[Acylation](/source/Acylation), the addition of an [acyl](/source/acyl) group (-C(O)R)
*[Deamination](/source/Deamination)

==References==
{{Reflist}}

Category:Organic reactions

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