Difference between revisions of "Hannah"
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| − | =Tautomers of Acetylacetone (C<sub>5</sub>H<sub>8</sub>O<sub>2</sub>)= | + | =Introduction= |
| + | ==Tautomers of Acetylacetone (C<sub>5</sub>H<sub>8</sub>O<sub>2</sub>)== | ||
| − | Keto = ketone | + | :-Keto = ketone |
| − | 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 | + | :-Usually the keto tautomer is favored |
| − | The basic reaction [[File:tautomerism.png|250px]] | + | :-The basic reaction [[File:tautomerism.png|250px]] |
==Why Tautomerization Matters== | ==Why Tautomerization Matters== | ||
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[[File:F1.large.jpg|500px]] | [[File:F1.large.jpg|500px]] | ||
| + | |||
| + | ==WebMO== | ||
| + | |||
| + | :-All calculations were done using HF/6-31G(d) | ||
==Keto Acetylacetone== | ==Keto Acetylacetone== | ||
[[File:molecule (2).png|200px]] | [[File:molecule (2).png|200px]] | ||
| − | Proton NMR | + | Proton NMR |
[[File:nmrKetoZoomed.png|400px]] | [[File:nmrKetoZoomed.png|400px]] | ||
| Line 32: | Line 37: | ||
[[File:molecule.png|200px]] | [[File:molecule.png|200px]] | ||
| − | Proton NMR | + | Proton NMR |
[[File:nmrEnol2.png|400px]] | [[File:nmrEnol2.png|400px]] | ||
Revision as of 20:54, 15 April 2021
Introduction
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)
WebMO
- -All calculations were done using HF/6-31G(d)
Keto Acetylacetone
.png)
Proton NMR
Proton NMR shifts:File:NMR-Chemical-Shift-PPM-Range-and-Values-Table-.png
Enol Acetylacetone
Proton NMR
Proton NMR shifts:File:NMR-Chemical-Shift-PPM-Range-and-Values-Table-.png
N.B. Hydrogen bonding deshields the proton, further increasing the chemical shift