Aminal

In organic chemistry, an aminal or aminoacetal is a functional group or type of organic compound that has two amine groups attached to the same carbon atom: −C(NR2)(NR2)−. (As is customary in organic chemistry, R can represent hydrogen or an alkyl group).[1] A common aminal is bis(dimethylamino)methane, a colorless liquid that is prepared by the reaction of dimethylamine and formaldehyde:[2]

2 (CH3)2NH + CH2O → [(CH3)2N]2CH2 + H2O

Aminals are encountered in, for instance, the Fischer indole synthesis. Several examples exist in nature.[3]

  • Naturally occurring aminals
  • Physostigmine,a highly toxic cholinesterase inhibitor found in the Calabar bean.
  • Hodgkinsine, an alkaloid with antiviral, antibacterial and antifungal effects
  • 5,10-Methylenetetrahydrofolate, an intermediate in one-carbon metabolism

Hexahydro-1,3,5-triazine ((CH2NH)3), an intermediate in the condensation of formaldehyde and ammonia, tends to degrade to hexamethylene tetraamine.

Cyclic aminals can be obtained by the condensation of a diamine and an aldehyde.[4] Imidazolidines are one class of these cyclic aminals.

See also

References
  1. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "aminals". doi:10.1351/goldbook.A00270
  2. Gaudry, Michel; Jasor, Yves; Khac, Trung Bui (1979). "Regioselective Mannich Condensation with Dimethyl(Methylene)ammonium Trifluoroacetate: 1-(Dimethylamino)-4-methyl-3-pentanone". Org. Synth. 59: 153. doi:10.15227/orgsyn.059.0153.
  3. Duhamel, Lucette (1982). "Aminals". In Saul Patai (ed.). Amino, Nitroso and Nitro Compounds and Their Derivatives: Vol. 2. PATAI'S Chemistry of Functional Groups. pp. 849–907. doi:10.1002/9780470771679.ch5. ISBN 9780470771679.
  4. Hiersemann, M. "Functions bearing two nitrogens" in Comprehensive Organic Functional Group Transformations II 2005, volume 4, 411-441. Edited by Katritzky, Alan R.; Taylor, Richard J. K. doi:10.1016/B0-08-044655-8/00075-1
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