tautomerism

Reversible structural interconversion

Tautomerism is a chemical phenomenon where a compound exists in two or more structural forms that readily convert between each other, usually by the movement of a hydrogen atom.

The different forms are called tautomers.

The most common type is keto-enol tautomerism, where a carbonyl compound shifts to a form with a hydroxyl group attached to a double bond.

The tautomerism of the molecule affects its reactivity.

types

keto-enol

Carbonyl-hydroxyl isomerism

structure

isomer

Same formula, different shape

equilibrium

dynamic equilibrium

Balance through opposing changes

applications

mutation

Permanent DNA alteration

Opposites
structural interconversion type

tautomerismresonance

Amplified oscillation at natural frequency

conjugation

Family

tautomeric

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