MC Chem Wiki - User contributions [en]

Hannah

2021-05-05T17:36:50Z

Hhofmann:

==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 (C5H8O2)===

:* Keto = ketone

:* Enol = alcohol
::-may also be referred to as an alkenol

:* Usually the keto tautomer is favored

{|
|[[File:tautomerism.png|thumbnail|Figure 1:Basic reaction of keto- and enol- acetylacetone]]
|}

===Why Tautomerization Matters===

:* 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

:* "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|thumbnail|Figure 2: Tautomers of nucleic acid bases]]
|}

==WebMO==

:*All calculations were done using HF/6-31G(d) for geometry optimization

:*The products of the geometry optimizations were used to calculate the NMR spectra using the same basis sets

==Keto Acetylacetone==
{|
|[[File:molecule (2).png|thumbnail|Figure 3: 3D structure of keto-acetylacetone]]
|}

Proton NMR
{|
|[[File:nmrKetoZoomed.png|thumbnail|Figure 4: Proton NMR for keto-acetylacetone]]
|}

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

==Enol Acetylacetone==
{|
|[[File:molecule.png|thumbnail| Figure 5: 3D structure of enol-acetylacetone]]
|}

Proton NMR
{|
|[[File:nmrEnol2.png|thumbnail| Figure 6: Proton NMR of enol-acetylacetone]]
|}

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

Hannah

2021-04-15T21:39:49Z

Hhofmann:

==Introduction==
===Tautomers of Acetylacetone (C5H8O2)===

:* Keto = ketone

:* Enol = alcohol
::-may also be referred to as an alkenol

:* Usually the keto tautomer is favored

{|
|[[File:tautomerism.png|thumbnail|Figure 1:Basic reaction of keto- and enol- acetylacetone]]
|}

===Why Tautomerization Matters===

:* 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

:* "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|thumbnail|Figure 2: Tautomers of nucleic acid bases]]
|}

==WebMO==

:*All calculations were done using HF/6-31G(d) for geometry optimization

:*The products of the geometry optimizations were used to calculate the NMR spectra using the same basis sets

==Keto Acetylacetone==
{|
|[[File:molecule (2).png|thumbnail|Figure 3: 3D structure of keto-acetylacetone]]
|}

Proton NMR
{|
|[[File:nmrKetoZoomed.png|thumbnail|Figure 4: Proton NMR for keto-acetylacetone]]
|}

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

==Enol Acetylacetone==
{|
|[[File:molecule.png|thumbnail| Figure 5: 3D structure of enol-acetylacetone]]
|}

Proton NMR
{|
|[[File:nmrEnol2.png|thumbnail| Figure 6: Proton NMR of enol-acetylacetone]]
|}

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

Hannah

2021-04-15T21:35:30Z

Hhofmann:

==Introduction==
===Tautomers of Acetylacetone (C5H8O2)===

:* Keto = ketone

:* Enol = alcohol
::-may also be referred to as an alkenol

:* Usually the keto tautomer is favored

{|
|[[File:tautomerism.png|thumbnail|Figure 1:Basic reaction of keto- and enol- acetylacetone]]
|}

===Why Tautomerization Matters===

:* 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

:* "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]]

==WebMO==

:*All calculations were done using HF/6-31G(d) for geometry optimization

:*The products of the geometry optimizations were used to calculate the NMR spectra using the same basis sets

==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

Hannah

2021-04-15T21:33:43Z

Hhofmann: /* Why Tautomerization Matters */

==Introduction==
===Tautomers of Acetylacetone (C5H8O2)===

:* Keto = ketone

:* Enol = alcohol
::-may also be referred to as an alkenol

:* Usually the keto tautomer is favored
[[File:tautomerism.png|thumbnail|Figure 1:Basic reaction of keto- and enol- acetylacetone]]

===Why Tautomerization Matters===

:* 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

:* "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]]

==WebMO==

:*All calculations were done using HF/6-31G(d) for geometry optimization

:*The products of the geometry optimizations were used to calculate the NMR spectra using the same basis sets

==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

Hannah

2021-04-15T21:32:15Z

Hhofmann: /* WebMO */

==Introduction==
===Tautomers of Acetylacetone (C5H8O2)===

:* Keto = ketone

:* Enol = alcohol
::-may also be referred to as an alkenol

:* Usually the keto tautomer is favored
[[File:tautomerism.png|thumbnail|Figure 1: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

:* "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]]

==WebMO==

:*All calculations were done using HF/6-31G(d) for geometry optimization

:*The products of the geometry optimizations were used to calculate the NMR spectra using the same basis sets

==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

Hannah

2021-04-15T21:29:05Z

Hhofmann:

Hannah

2021-04-15T21:27:33Z

Hhofmann:

Hannah

2021-04-15T21:23:30Z

Hhofmann: /* Enol Acetylacetone */

==Introduction==
===Tautomers of Acetylacetone (C5H8O2)===

:-Keto = ketone

:-Enol = alcohol
::-may also be referred to as an alkenol

:-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

:-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)

[[File:F1.large.jpg|500px]]

==WebMO==

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

==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

Hannah

2021-04-15T21:23:22Z

Hhofmann: /* Keto Acetylacetone */

==Introduction==
===Tautomers of Acetylacetone (C5H8O2)===

:-Keto = ketone

:-Enol = alcohol
::-may also be referred to as an alkenol

:-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

:-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)

[[File:F1.large.jpg|500px]]

==WebMO==

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

==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

Hannah

2021-04-15T21:23:09Z

Hhofmann: /* WebMO */

==Introduction==
===Tautomers of Acetylacetone (C5H8O2)===

:-Keto = ketone

:-Enol = alcohol
::-may also be referred to as an alkenol

:-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

:-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)

[[File:F1.large.jpg|500px]]

==WebMO==

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

=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

Hannah

2021-04-15T21:22:59Z

Hhofmann: /* Introduction */

==Introduction==
===Tautomers of Acetylacetone (C5H8O2)===

:-Keto = ketone

:-Enol = alcohol
::-may also be referred to as an alkenol

:-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

:-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)

[[File:F1.large.jpg|500px]]

=WebMO=

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

=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

Hannah

2021-04-15T21:12:47Z

Hhofmann: /* Introduction */

=Introduction=
==Tautomers of Acetylacetone (C5H8O2)==

:-Keto = ketone

:-Enol = alcohol
::-may also be referred to as an alkenol

:-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

:-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)

[[File:F1.large.jpg|500px]]

=WebMO=

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

=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

Hannah

2021-04-15T21:12:03Z

Hhofmann: /* Introduction */

=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: [[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

:-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)

[[File:F1.large.jpg|500px]]

=WebMO=

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

=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

Hannah

2021-04-15T21:10:51Z

Hhofmann: /* Introduction */

=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: [[File:tautomerism.png|250px|basic]]

==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)

[[File:F1.large.jpg|500px]]

=WebMO=

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

=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

Hannah

2021-04-15T21:00:13Z

Hhofmann: /* Introduction */

=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: [[File:tautomerism.png|250px]]

==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)

[[File:F1.large.jpg|500px]]

=WebMO=

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

=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

File:ImageForArticle 12317(1).jpg

2021-04-15T20:57:10Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

File:Acetyloaceton.svg.png

2021-04-15T20:55:50Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

Hannah

2021-04-15T20:54:22Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=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 [[File:tautomerism.png|250px]]

==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)

[[File:F1.large.jpg|500px]]

==WebMO==

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

==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

Hannah

2021-04-15T20:42:42Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=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 [[File:tautomerism.png|250px]]

==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)

[[File:F1.large.jpg|500px]]

==Keto Acetylacetone==
[[File:molecule (2).png|200px]]

Proton NMR (Hartree-Fock)

[[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 (Hartree-Fock)

[[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

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

2021-04-15T20:34:30Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

Hannah

2021-04-15T20:32:12Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=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 [[File:tautomerism.png|250px]]

==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)

[[File:F1.large.jpg|500px]]

==Keto Acetylacetone==
[[File:molecule (2).png|200px]]

Proton NMR (Hartree-Fock)

[[File:nmrKetoZoomed.png|400px]]

Proton NMR shifts: [[:File:NMRshifts1H-general.pdf]]

==Enol Acetylacetone==
[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)

[[File:nmrEnol2.png|400px]]

Proton NMR shifts: [[:File:NMRshifts1H-general.pdf]]

Hannah

2021-04-15T20:31:43Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=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 [[File:tautomerism.png|250px]]

==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)

[[File:F1.large.jpg|500px]]

==Keto Acetylacetone==
[[File:molecule (2).png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrKetoZoomed.png|400px]]

Proton NMR shifts: [[:File:NMRshifts1H-general.pdf]]

==Enol Acetylacetone==
[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrEnol2.png|400px]]

Proton NMR shifts: [[:File:NMRshifts1H-general.pdf]]

File:NMRshifts1H-general.pdf

2021-04-15T20:31:01Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

Hannah

2021-04-15T20:23:00Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol

The basic reaction [[File:tautomerism.png|250px]]

==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)
[[File:F1.large.jpg|500px]]

==Keto Acetylacetone==
With geometry optimization [[File:molecule (2).png|200px]]

:PubChem's 3D structure has both oxygens pointing in the same direction (left) while NIST has the oxygens pointing in different directions (right)

:[[File:Acetylacetone_400×300_3D_Conformer.png|200px]] [[File:ketoacetylacetoneStructure.png|150px]]

Proton NMR (Hartree-Fock)
[[File:nmrKetoZoomed.png|400px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrEnol2.png|400px]]

Hannah

2021-04-15T20:20:49Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol

The basic reaction [[File:tautomerism.png|250px]]

==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

-A greater diversity of nucleic acid bases [[File:F1.large.jpg|500px]]

==Keto Acetylacetone==
With geometry optimization [[File:molecule (2).png|200px]]

:PubChem's 3D structure has both oxygens pointing in the same direction (left) while NIST has the oxygens pointing in different directions (right)

:[[File:Acetylacetone_400×300_3D_Conformer.png|200px]] [[File:ketoacetylacetoneStructure.png|150px]]

Proton NMR (Hartree-Fock)
[[File:nmrKetoZoomed.png|400px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrEnol2.png|400px]]

File:F1.large.jpg

2021-04-15T20:20:37Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

Hannah

2021-04-15T20:19:58Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol

The basic reaction [[File:tautomerism.png|250px]]

==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

-A greater diversity of nucleic acid bases [[File:RNA2.gif|400px]]

==Keto Acetylacetone==
With geometry optimization [[File:molecule (2).png|200px]]

:PubChem's 3D structure has both oxygens pointing in the same direction (left) while NIST has the oxygens pointing in different directions (right)

:[[File:Acetylacetone_400×300_3D_Conformer.png|200px]] [[File:ketoacetylacetoneStructure.png|150px]]

Proton NMR (Hartree-Fock)
[[File:nmrKetoZoomed.png|400px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrEnol2.png|400px]]

File:RNA2.gif

2021-04-15T20:19:47Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

Hannah

2021-04-15T20:19:09Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol

The basic reaction [[File:tautomerism.png|250px]]

==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
-A greater diversity of nucleic acid bases [[File:RNA.gif|400px]]

==Keto Acetylacetone==
With geometry optimization [[File:molecule (2).png|200px]]

:PubChem's 3D structure has both oxygens pointing in the same direction (left) while NIST has the oxygens pointing in different directions (right)

:[[File:Acetylacetone_400×300_3D_Conformer.png|200px]] [[File:ketoacetylacetoneStructure.png|150px]]

Proton NMR (Hartree-Fock)
[[File:nmrKetoZoomed.png|400px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrEnol2.png|400px]]

File:RNA.gif

2021-04-15T20:18:56Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

Hannah

2021-04-15T20:08:46Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol

The basic reaction [[File:tautomerism.png|200px]]

==Keto Acetylacetone==
With geometry optimization [[File:molecule (2).png|200px]]

:PubChem's 3D structure has both oxygens pointing in the same direction (left) while NIST has the oxygens pointing in different directions (right)

:[[File:Acetylacetone_400×300_3D_Conformer.png|200px]] [[File:ketoacetylacetoneStructure.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrKetoZoomed.png|400px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrEnol2.png|400px]]

File:Tautomerism.png

2021-04-15T20:08:21Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

Hannah

2021-04-15T20:01:29Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|200px]]

:PubChem's 3D structure has both oxygens pointing in the same direction (left) while NIST has the oxygens pointing in different directions (right)

:[[File:Acetylacetone_400×300_3D_Conformer.png|200px]] [[File:ketoacetylacetoneStructure.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrKetoZoomed.png|400px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrEnol2.png|400px]]

Hannah

2021-04-15T19:50:12Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|200px]]

:PubChem's 3D structure has both oxygens pointing in the same direction (left) while NIST has the oxygens pointing in different directions (right)

:[[File:Acetylacetone_400×300_3D_Conformer.png|200px]] [[File:ketoacetylacetoneStructure.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrKetoZoomed.png|400px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)
[[File:nmrEnol2.png|400px]]
[[File:nmrEnolZoomed.png|400px]]

File:NmrEnolZoomed.png

2021-04-15T19:50:00Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

File:NmrEnol2.png

2021-04-15T19:48:50Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

File:NmrKetoZoomed.png

2021-04-15T19:47:40Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

Hannah

2021-04-15T19:17:02Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|200px]]

:PubChem's 3D structure has both oxygens pointing in the same direction (left) while NIST has the oxygens pointing in different directions (right)

:[[File:Acetylacetone_400×300_3D_Conformer.png|200px]] [[File:ketoacetylacetoneStructure.png|200px]]

Proton NMR (Hartree-Fock)
:A reminder of Proton NMR stretches: [[:File:nmr1.gif]]

[[File:nmrKeto.png|300px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)
:A reminder of Proton NMR stretches: [[:File:nmr1.gif]]

[[File:nmrEnol.png|300px]]

Hannah

2021-04-15T19:12:19Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|200px]]

:But PubChem's 3D structure has both oxygens pointing in the same direction

:[[File:Acetylacetone_400×300_3D_Conformer.png|200px]]

:But NIST has the oxygens pointing different directions

:[[File:ketoacetylacetoneStructure.png|200px]]

Proton NMR (Hartree-Fock)
:A reminder of Proton NMR stretches: [[:File:nmr1.gif]]

[[File:nmrKeto.png|300px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)
:A reminder of Proton NMR stretches: [[:File:nmr1.gif]]

[[File:nmrEnol.png|300px]]

Hannah

2021-04-15T18:29:38Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|200px]]

But PubChem's 3D structure has both oxygens pointing in the same direction

[[File:Acetylacetone_400×300_3D_Conformer.png|200px]]

But NIST has the oxygens pointing different directions

[[File:ketoacetylacetoneStructure.png|200px]]

Proton NMR (Hartree-Fock)

[[File:nmrKeto.png|300px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)

[[File:nmrEnol.png|300px]]

A reminder of Proton NMR stretches:
[[:File:nmr1.gif]]

File:Nmr1.gif

2021-04-15T18:29:32Z

Hhofmann: Hhofmann uploaded a new version of File:Nmr1.gif

File uploaded with MsUpload

Hannah

2021-04-15T18:29:13Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|200px]]

But PubChem's 3D structure has both oxygens pointing in the same direction

[[File:Acetylacetone_400×300_3D_Conformer.png|200px]]

But NIST has the oxygens pointing different directions

[[File:ketoacetylacetoneStructure.png|200px]]

Proton NMR (Hartree-Fock)

[[File:nmrKeto.png|300px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)

[[File:nmrEnol.png|300px]]

A reminder of Proton NMR stretches:

[[File:nmr1.gif|500px]]

Hannah

2021-04-15T18:28:37Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|200px]]

But PubChem's 3D structure has both oxygens pointing in the same direction

[[File:Acetylacetone_400×300_3D_Conformer.png|200px]]

But NIST has the oxygens pointing different directions

[[File:ketoacetylacetoneStructure.png|200px]]

Proton NMR (Hartree-Fock)

[[File:nmrKeto.png|200px]]

==Enol Acetylacetone==

[[File:molecule.png|200px]]

Proton NMR (Hartree-Fock)

[[File:nmrEnol.png|300px]]

A reminder of Proton NMR stretches:

[[File:nmr1.gif|300px]]

File:Nmr1.gif

2021-04-15T18:28:27Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

Hannah

2021-04-15T18:19:07Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|300px]]

But PubChem's 3D structure has both oxygens pointing in the same direction

[[File:Acetylacetone_400×300_3D_Conformer.png|300px]]

But NIST has the oxygens pointing different directions

[[File:ketoacetylacetoneStructure.png|200px]]

Proton NMR (Hartree-Fock)

[[File:nmrKeto.png|300px]]

==Enol Acetylacetone==

[[File:molecule.png|300px]]

Proton NMR (Hartree-Fock)

[[File:nmrEnol.png|300px]]

Hannah

2021-04-15T18:16:55Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|300px]]

But PubChem's 3D structure has both oxygens pointing in the same direction

[[File:Acetylacetone_400×300_3D_Conformer.png|300px]]

But NIST has the oxygens pointing different directions

[[File:ketoacetylacetoneStructure.png|300px]]

Proton NMR (Hartree-Fock)

[[File:nmrKeto.png|300px]]

==Enol Acetylacetone==

[[File:molecule.png|300px]]

Proton NMR (Hartree-Fock)

[[File:nmrEnol.png|300px]]

File:KetoacetylacetoneStructure.png

2021-04-15T18:16:46Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload

Hannah

2021-04-15T18:15:06Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored

Keto = ketone

Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|300px]]

PubChem's 3D structure has both oxygens pointing in the same direction

[[File:Acetylacetone_400×300_3D_Conformer.png|300px]]

Proton NMR (Hartree-Fock)

[[File:nmrKeto.png|300px]]

==Enol Acetylacetone==

[[File:molecule.png|300px]]

Proton NMR (Hartree-Fock)

[[File:nmrEnol.png|300px]]

Hannah

2021-04-15T18:14:28Z

Hhofmann: /* Tautomers of Acetylacetone (C5H8O2) */

=Tautomers of Acetylacetone (C5H8O2)=
Usually the keto tautomer is favored
Keto = ketone
Enol = alcohol
:may also be referred to as an alkenol
==Keto Acetylacetone==
With geometry optimization

[[File:molecule (2).png|300px]]

PubChem's 3D structure has both oxygens pointing in the same direction

[[File:Acetylacetone_400×300_3D_Conformer.png|300px]]

Proton NMR (Hartree-Fock)

[[File:nmrKeto.png|300px]]

==Enol Acetylacetone==

[[File:molecule.png|300px]]

Proton NMR (Hartree-Fock)

[[File:nmrEnol.png|300px]]

File:NmrEnol.png

2021-04-15T18:14:08Z

Hhofmann: File uploaded with MsUpload

File uploaded with MsUpload