Difference between revisions of "Hannah"
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| − | =Introduction= | + | ==Introduction== |
| − | ==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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[[File:tautomerism.png|thumbnail|The basic reaction of keto- and enol- acetylacetone]] | [[File:tautomerism.png|thumbnail|The basic reaction of keto- and enol- acetylacetone]] | ||
| − | ==Why Tautomerization Matters== | + | ===Why Tautomerization Matters=== |
:-Different solvents may change the equilibrium of the keto- and enol- forms | :-Different solvents may change the equilibrium of the keto- and enol- forms | ||
Revision as of 21:22, 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
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