Difference between revisions of "Hannah"
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==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 |
| − | -Tautomers in DNA replication have been hypothesized to contribute to mutagenic mispairings | + | :-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) | + | :-"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]] | ||
| Line 27: | Line 27: | ||
[[File:nmrKetoZoomed.png|400px]] | [[File:nmrKetoZoomed.png|400px]] | ||
| − | Proton NMR shifts: [[:File: | + | Proton NMR shifts:[[:File:NMR-Chemical-Shift-PPM-Range-and-Values-Table-.png]] |
==Enol Acetylacetone== | ==Enol Acetylacetone== | ||
| Line 36: | Line 36: | ||
[[File:nmrEnol2.png|400px]] | [[File:nmrEnol2.png|400px]] | ||
| − | Proton NMR shifts: [[:File: | + | 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 | ||
Revision as of 20:42, 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:NMR-Chemical-Shift-PPM-Range-and-Values-Table-.png
Enol Acetylacetone
Proton NMR (Hartree-Fock)
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