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Tautomer
Structural isomers of chemical compounds that readily interconvert / From Wikipedia, the free encyclopedia
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Tautomers (/ˈtɔːtəmər/)[1] are structural isomers (constitutional isomers) of chemical compounds that readily interconvert.[2][3][4][5] 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.
![An amino acid, illustrated in two different ionization states. First, it has a neutral amine and neutral carboxylic acid. Second, it has a protonated ammonium cation and deprotonated carboxylate anion.](http://upload.wikimedia.org/wikipedia/commons/thumb/d/de/Amino_acid_zwitterions.svg/320px-Amino_acid_zwitterions.svg.png)
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,[6] 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.