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Concept
Tautomer
Summary
Tautomers (ˈtɔːtəmɚ
) are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life.
Care should be taken not to confuse tautomers with depictions of "contributing structures" in chemical resonance. Tautomers are distinct chemical species that can be distinguished by their differing atomic connectivities, molecular geometries, and physicochemical and spectroscopic properties, whereas resonance forms are merely alternative Lewis structure (valence bond theory) depictions of a single chemical species, whose true structure is a quantum superposition, essentially the "average" of the idealized, hypothetical geometries implied by these resonance forms.
Tautomerization is pervasive in organic chemistry. It is typically associated with polar molecules and ions containing functional groups that are at least weakly acidic. Most common tautomers exist in pairs, which means that the hydrogen is located at one of two positions, and even more specifically the most common form involves a hydrogen changing places with a double bond: . Common tautomeric pairs include:
ketone – enol: , see keto–enol tautomerism
enamine – imine:
cyanamide – carbodiimide
guanidine – guanidine – guanidine: With a central carbon surrounded by three nitrogens, a guanidine group allows this transform in three possible orientations
amide – imidic acid: (e.g., the latter is encountered during nitrile hydrolysis reactions)
lactam – lactim, a cyclic form of amide-imidic acid tautomerism in 2-pyridone and derived structures such as the nucleobases guanine, thymine, and cytosine
imine – imine, e.g.
Official source
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