organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

, imidic acids are

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

s with the structure . They are tautomeric to non- tertiary amides () and

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

ic to oximes (). The term " imino acid" is an obsolete term for this group that should not be used in this context because it has a different molecular structure.{{GoldBookRef , file=I02959 , title=Imino acids , accessdate=2012-04-02 Imidic acids can be formed by metal-catalyzed dehydrogenation of geminal amino alcohols. For example, methanolamine, the parent compound of the amino alcohols, can be dehydrogenated to methanimidic acid, the parent compound of the imidic acids. :H₂NCH₂OH → HNCHOH + H₂ (tautomer of formamide) Geminal amino alcohols with side chains similarly form imidic acids with the same side chains: :H₂NCHROH → HNCROH + H₂ Another way to form imidic acids is the reaction of carboxylic acids with azanone. For example, the reaction for

carbamic acid Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula . It can be obtained by the reaction of ammonia and carbon dioxide at very low temperatures, which also yields ammoni ...

: :H₂NCOOH + HNO → H₂NCNHOH + O₂ (tautomer of

urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

) And the general reaction for substituted imidic acids: :RCOOH + R'NO → RCNR'OH + O₂ Another mechanism is the reaction of carboxylic acids with diazene or other azo compounds, forming azanone. :RCOOH + HNNH → RCNHOH + HNO Imidic acids tautomerize to amides by a hydrogen shift from the oxygen to the nitrogen atom. Amides are more stable in an environment with oxygen or water, whereas imidic acids dominate the equilibrium in solution with ammonia or methane. :HNCHOH ⇌ HCONH₂ :RNCR'OH ⇌ R'CONHR

References

Amides Functional groups

See also

References