Difference between revisions of "Hannah"
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=Tautomers of Acetylacetone (C<sub>5</sub>H<sub>8</sub>O<sub>2</sub>)= | =Tautomers of Acetylacetone (C<sub>5</sub>H<sub>8</sub>O<sub>2</sub>)= | ||
| − | |||
Keto = ketone | Keto = ketone | ||
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Enol = alcohol | Enol = alcohol | ||
:may also be referred to as an alkenol | :may also be referred to as an alkenol | ||
| + | |||
| + | Usually the keto tautomer is favored | ||
The basic reaction [[File:tautomerism.png|250px]] | The basic reaction [[File:tautomerism.png|250px]] | ||
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-"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) | -"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) | ||
| + | |||
[[File:F1.large.jpg|500px]] | [[File:F1.large.jpg|500px]] | ||
==Keto Acetylacetone== | ==Keto Acetylacetone== | ||
| − | + | [[File:molecule (2).png|200px]] | |
| − | |||
| − | |||
| − | |||
| − | |||
Proton NMR (Hartree-Fock) | Proton NMR (Hartree-Fock) | ||
[[File:nmrKetoZoomed.png|400px]] | [[File:nmrKetoZoomed.png|400px]] | ||
| + | |||
| + | Proton NMR shifts: [[:File:NMRshifts1H-general.pdf]] | ||
==Enol Acetylacetone== | ==Enol Acetylacetone== | ||
| − | |||
[[File:molecule.png|200px]] | [[File:molecule.png|200px]] | ||
Proton NMR (Hartree-Fock) | Proton NMR (Hartree-Fock) | ||
[[File:nmrEnol2.png|400px]] | [[File:nmrEnol2.png|400px]] | ||
| + | |||
| + | Proton NMR shifts: [[:File:NMRshifts1H-general.pdf]] | ||
Revision as of 20:31, 15 April 2021
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 
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
.png)
Proton NMR (Hartree-Fock)
Proton NMR shifts: File:NMRshifts1H-general.pdf
Enol Acetylacetone
Proton NMR (Hartree-Fock)
Proton NMR shifts: File:NMRshifts1H-general.pdf