Difference between revisions of "Hannah"

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===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
  
:-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
 
[[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
  
:-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)
  
  
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==WebMO==
 
==WebMO==
  
:-All calculations were done using HF/6-31G(d)
+
:*All calculations were done using HF/6-31G(d)
  
 
==Keto Acetylacetone==
 
==Keto Acetylacetone==

Revision as of 21:27, 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 of keto- and enol- acetylacetone

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


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