Tautomer
Tautomers are constitutional isomers of organic compounds that readily interconvert with each other. The chemical reaction interconverting the two is called tautomerization. This reaction commonly results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond. The concept of tautomerizations is called tautomerism. Because of the rapid interconversion, tautomers are generally considered to be the same chemical compound. Tautomerism is a special case of structural isomerism and can play an important role in non-canonical base pairing in DNA and especially RNA molecules.
Chemistry
In solutions in which tautomerization is possible, a chemical equilibrium of the tautomers will be reached. The exact ratio of the tautomers depends on several factors, including temperature, solvent, and pH.
Common tautomeric pairs include:
ketone - enol, e.g., for acetone (see: keto–enol tautomerism);
enamine - imine;
ketene - ynol, e.g., for ethenone;