Hannah

Tautomers of Acetylacetone (C₅H₈O₂)

Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol

may also be referred to as an alkenol

The basic reaction

Why Tautomerization Matters

-Different solvents may change the equilibrium of the keto- and enol- forms

-Tautomers in DNA replication have been hypothesized to contribute to mutagenic mispairings

-"whereas in RNA, minor tautomeric forms have been proposed to enhance the structural and functional diversity of RNA enzymes and aptamers" (https://rnajournal.cshlp.org/content/21/1/1.full.html)

Keto Acetylacetone

With geometry optimization

PubChem's 3D structure has both oxygens pointing in the same direction (left) while NIST has the oxygens pointing in different directions (right)

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Proton NMR (Hartree-Fock)

Enol Acetylacetone

Proton NMR (Hartree-Fock)