Definitions

tautomerism

tautomerism

[taw-tom-uh-riz-uhm]

Existence of two or more chemical compounds that have the same chemical composition but different structures (isomers) and that convert easily from one to another. A major class of tautomeric reactions involves exchange of a hydrogen atom between two other atoms in the same molecule, in both cases forming a covalent bond. For example, in keto-enol tautomerism, the hydrogen atom bonded to the carbon atom in a carbonyl (keto) group (singlehorzbondCHsinglehorzbondCdoublehorzbondO; see functional group) moves to the oxygen atom, making it an enol group (singlehorzbondCdoublehorzbondCsinglehorzbondOH). The keto form predominates in many aldehydes and ketones, the enol form in phenols. Sugars (e.g., glucose) exhibit tautomerism between open (chain) forms and closed (ring) forms. Seealso isomerism.

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