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.
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "aminals". doi:10.1351/goldbook.A00270
^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.
^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.
^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
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...
Funny Aminals is a 1972 single-issue anthology underground comic book created by Robert Crumb and a collection of other artists. The work is notable for...
alkylimino-de-oxo-bisubstitution. Hemiaminals can be viewed as a blend of aminals and geminal diol. They are a special case of amino alcohols. Hemiaminals...
proceeds to the mixed aminal/carbinolamine 4; such a product would be expected to be in equilibrium with the alternate aminal 5. The latter would be...
which can react with a second equivalent of the secondary amine to form aminals. At increased temperatures, pyridines including DMAP, react with DCM to...
takes place between an aldehyde or ketone and a primary amine. Similarly, aminal formation takes place between an aldehyde or ketone and a vicinal secondary...
of type R1R2C(OR)(NR'2) (R,R' ≠ H) also known as a hemiaminal ether or Aminal, a.k.a. aminoacetal. S,S-acetal refers to compounds of type R1R2C(SR)(SR')...
producing a diimine. The resulting diimine forms a cyclic aminoacetal (or aminal), which under acid catalysis eliminates NH3, resulting in the energetically...
States Traditional Barnyard Babies United States Traditional Be Kind to "Aminals" United States Traditional Betty Boop and Grampy United States Traditional...
cartoons : Hare Conditioned (1945), That's My Mommy (1955), Be Kind to 'Aminals' (1935), Muzzle Tough (1954), The Ducksters (1950) 21 21 "Two Drink Minimum...
Ls as well as Ms and Ns, mixing up sounds in multi-syllabic words (ex: aminal for animal, spahgetti for spaghetti, heilcopter for helicopter, hangaberg...
task of the continuation of the publication yet). Nural-Qur'an by Muhammad Aminal-Islam (30 volumes) (1981-1998) Tafsir al-Quran by Delwar Hossain Sayidi...
also a Lewis base. It reacts with many carbonyl compounds. Aldehydes give aminals. For example reaction of dimethylamine and formaldehyde gives bis(dimethylamino)methane:...
2-(2-methoxyethoxy)acetaldehyde. The 9N, 11O-oxazine ring thus formed is a hemi-aminal that is unstable under both acidic and alkaline aqueous conditions and undergoes...
conditions. The final step is based on the intramolecular cyclization of an aminal. Unsubstituted diaziridines are often directly oxidized (I2/NEt3) to the...
Anthracyclines can also form adducts with DNA by a single covalent bond through an aminal linkage from the 3’-amino of daunosamine to the exocyclic amino of guanine...
Lines" Division Day 2000s Indie Rock Apr 12, 2010 No No "Drag Me Away" Aminal 2000s Indie Rock Apr 12, 2010 No No "Eden was a Garden" Roman Candle 2000s...
Spiegelman to contribute a three-page strip for the first issue of Funny Aminals, which Green edited. Spiegelman wanted to do a strip about racism, and...
bank was first proposed by Haj Mohammad Hassan Amin Dar al-Zarb known as Amināl-Zarb (one of the Tehran stockholders) in 1879 ten years before the creation...
existed around his garden. A heavily converted Motor Rail (later named Aminal [sic.]) was acquired from a nearby brickworks. This, alongside coaches built...
from a three-page story first published in an underground comic, Funny Aminals [sic], (Apex Novelties, 1972). Alternative cartoonist Peter Bagge was strongly...
in the underground comix scene. He initially edited the one-shot Funny Aminals #1 (Apex Novelties, 1972), the groundbreaking comic in which Art Spiegelman...
not have a proton available and instead they often react further to an aminal: or when an α-carbonyl proton is present to an enamine: In acidic environment...
Global Information
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
