Hannah - Revision history

Hhofmann at 17:36, 5 May 2021

2021-05-05T17:36:50Z

2021-04-15T21:39:49Z

2021-04-15T21:35:30Z

2021-04-15T21:33:43Z

Why Tautomerization Matters

2021-04-15T21:32:15Z

WebMO

2021-04-15T21:29:05Z

2021-04-15T21:27:33Z

2021-04-15T21:23:30Z

Enol Acetylacetone

2021-04-15T21:23:22Z

Keto Acetylacetone

2021-04-15T21:23:09Z

WebMO

← Older revision		Revision as of 17:36, 5 May 2021
Line 1:		Line 1:
	==Introduction==		==Introduction==
		+
		+	Based on Experiment 44: NMR determination of keto-enol equilibrium constants p522
		+
		+	Shoemaker, D. P., Garland, C. W., & Nibler, J. W. (1989). Experiments in physical chemistry (5. ed). McGraw Hill.
		+
	===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>)===

@@ Line 23: / Line 23: @@
 :* "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|thumbnail|Figure 2: Tautomers of nucleic acid bases]]
 ==WebMO==
@@ Line 33: / Line 34: @@
 ==Keto Acetylacetone==
-[[File:molecule (2).png|200px]]
+{|
 Proton NMR
-[[File:nmrKetoZoomed.png|400px]]
+{|
 Proton NMR shifts:[[:File:NMR-Chemical-Shift-PPM-Range-and-Values-Table-.png]]
 ==Enol Acetylacetone==
-[[File:molecule.png|200px]]
+{|
 Proton NMR
-[[File:nmrEnol2.png|400px]]
+{|
 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

@@ Line 8: / Line 8: @@
 :* Usually the keto tautomer is favored
 [[File:tautomerism.png|thumbnail|Figure 1:Basic reaction of keto- and enol- acetylacetone]]
 ===Why Tautomerization Matters===

← Older revision		Revision as of 21:33, 15 April 2021
Line 13:		Line 13:

	:* Different solvents may change the equilibrium of the keto- and enol- forms		:* Different solvents may change the equilibrium of the keto- and enol- forms
		+
		+	::-Keto/enol equilibrium can be determined using proton NMR, as the spectra are different enough to distinguish between the tautomers

	:* Tautomers in DNA replication have been hypothesized to contribute to mutagenic mispairings		:* Tautomers in DNA replication have been hypothesized to contribute to mutagenic mispairings

@@ Line 23: / Line 23: @@
 ==WebMO==
-:*All calculations were done using HF/6-31G(d)
+:*All calculations were done using HF/6-31G(d) for geometry optimization
 ==Keto Acetylacetone==

@@ Line 2: / Line 2: @@
 ===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
-:-Usually the keto tautomer is favored
+:* Usually the keto tautomer is favored
 [[File:tautomerism.png|thumbnail|The basic reaction of keto- and enol- acetylacetone]]
 ===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)
@@ Line 23: / Line 23: @@
 ==WebMO==
-:-All calculations were done using HF/6-31G(d)
+:*All calculations were done using HF/6-31G(d)
 ==Keto Acetylacetone==