Tautomerizes

Tautomerizes is the third person singular present tense of tautomerize, meaning to undergo tautomerization. Tautomerization is a chemical process in which a compound rearranges to a different constitutional isomer (a tautomer) through rapid proton transfer and accompanying shift of a multiple bond. The equilibrium exists between tautomers and often lies along a continuum depending on solvent, temperature, and pH. The interconversion is usually rapid on the timescale of many reactions.

The best-known example is keto-enol tautomerism, where a carbonyl compound converts to its enol form. Other forms include imine-enamine tautomerism and lactam-lactim tautomerism in heterocyclic compounds. Many biologically relevant molecules exhibit tautomerization; for example, certain nitrogen-containing heterocycles and nucleobases can interchange tautomers under physiological conditions. Some tautomerizations are intramolecular, others involve solvent participation or catalysis.

Mechanistic aspects: Proton transfer and reorganization of π bonds; acid or base catalysis can accelerate the process; solvent polarity and hydrogen-bonding networks influence the equilibrium position. The two (or more) tautomers are constitutional isomers whose interconversion alters properties such as acidity, basicity, UV/visible spectra, and reactivity.

Significance: Tautomerization affects synthesis planning, reaction outcomes, and interpretation of spectroscopic data; in medicinal chemistry, tautomeric form can influence binding and activity. In chemical literature, the verb tautomerizes is used to describe molecules undergoing this rearrangement.