Hannah

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Tautomers of Acetylacetone (C5H8O2)

Keto = ketone

Enol = alcohol

may also be referred to as an alkenol

Usually the keto tautomer is favored

The basic reaction Tautomerism.png

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)

F1.large.jpg

Keto Acetylacetone

Molecule (2).png

Proton NMR (Hartree-Fock)

NmrKetoZoomed.png

Proton NMR shifts: File:NMRshifts1H-general.pdf

Enol Acetylacetone

Molecule.png

Proton NMR (Hartree-Fock)

NmrEnol2.png

Proton NMR shifts: File:NMRshifts1H-general.pdf