Difference between revisions of "Hannah"
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:* Usually the keto tautomer is favored | :* Usually the keto tautomer is favored | ||
| − | [[File:tautomerism.png|thumbnail| | + | [[File:tautomerism.png|thumbnail|Figure 1:Basic reaction of keto- and enol- acetylacetone]] |
===Why Tautomerization Matters=== | ===Why Tautomerization Matters=== | ||
Revision as of 21:29, 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