Difference between revisions of "Hannah"

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:-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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:-"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]]
  
==WebMO==
+
=WebMO=
  
 
:-All calculations were done using HF/6-31G(d)
 
:-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]]
  
 
Proton NMR shifts:[[:File:NMR-Chemical-Shift-PPM-Range-and-Values-Table-.png]]
 
Proton NMR shifts:[[:File:NMR-Chemical-Shift-PPM-Range-and-Values-Table-.png]]
  
==Enol Acetylacetone==
+
=Enol Acetylacetone=
 
[[File:molecule.png|200px]]
 
[[File:molecule.png|200px]]
  
 
Proton NMR
 
Proton NMR
 
 
[[File:nmrEnol2.png|400px]]
 
[[File:nmrEnol2.png|400px]]
  

Revision as of 21:00, 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: Tautomerism.png

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)


F1.large.jpg

WebMO

-All calculations were done using HF/6-31G(d)

Keto Acetylacetone

Molecule (2).png

Proton NMR NmrKetoZoomed.png

Proton NMR shifts:File:NMR-Chemical-Shift-PPM-Range-and-Values-Table-.png

Enol Acetylacetone

Molecule.png

Proton NMR NmrEnol2.png

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