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N,N-Dimethylacetamide

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Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
RCD - Robert C. Dunbar
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

C3H10N+ + N,N-Dimethylacetamide = (C3H10N+ bullet N,N-Dimethylacetamide)

By formula: C3H10N+ + C4H9NO = (C3H10N+ bullet C4H9NO)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Deltar114.kJ/molPHPMSMeot-Ner, 1984gas phase; M
Deltar114.kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Deltar101.J/mol*KPHPMSMeot-Ner, 1984gas phase; M
Deltar101.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

C4H8NO- + Hydrogen cation = N,N-Dimethylacetamide

By formula: C4H8NO- + H+ = C4H9NO

Quantity Value Units Method Reference Comment
Deltar1568. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1540. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C4H10NO+ + N,N-Dimethylacetamide = (C4H10NO+ bullet N,N-Dimethylacetamide)

By formula: C4H10NO+ + C4H9NO = (C4H10NO+ bullet C4H9NO)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Deltar131.kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Deltar115.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

Potassium ion (1+) + N,N-Dimethylacetamide = (Potassium ion (1+) bullet N,N-Dimethylacetamide)

By formula: K+ + C4H9NO = (K+ bullet C4H9NO)

Quantity Value Units Method Reference Comment
Deltar121.kJ/molCIDTKlassen, Anderson, et al., 1996RCD
Deltar130.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar96.J/mol*KHPMSSunner, 1984gas phase; M

(Potassium ion (1+) bullet 2N,N-Dimethylacetamide) + N,N-Dimethylacetamide = (Potassium ion (1+) bullet 3N,N-Dimethylacetamide)

By formula: (K+ bullet 2C4H9NO) + C4H9NO = (K+ bullet 3C4H9NO)

Quantity Value Units Method Reference Comment
Deltar75.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar100.J/mol*KHPMSSunner, 1984gas phase; M

(Potassium ion (1+) bullet N,N-Dimethylacetamide) + N,N-Dimethylacetamide = (Potassium ion (1+) bullet 2N,N-Dimethylacetamide)

By formula: (K+ bullet C4H9NO) + C4H9NO = (K+ bullet 2C4H9NO)

Quantity Value Units Method Reference Comment
Deltar100.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar100.J/mol*KHPMSSunner, 1984gas phase; M

N,N-Dimethylacetamide = Ethanimidic acid, N-methyl-, methyl ester

By formula: C4H9NO = C4H9NO

Quantity Value Units Method Reference Comment
Deltar67. ± 3.kJ/molEqkBeak, Lee, et al., 1978liquid phase; ALS

Sodium ion (1+) + N,N-Dimethylacetamide = (Sodium ion (1+) bullet N,N-Dimethylacetamide)

By formula: Na+ + C4H9NO = (Na+ bullet C4H9NO)

Quantity Value Units Method Reference Comment
Deltar157.kJ/molCIDTKlassen, Anderson, et al., 1996RCD

References

Go To: Top, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Meot-Ner, 1984, 2
Meot-Ner, (Mautner), The Ionic Hydrogen Bond. 4. Intramolecular and Multiple Bonds. Proton Affinities, Hydration and Complexes of Amides and Amino Acid Derivatives, J. Am. Chem. Soc., 1984, 106, 2, 278, https://doi.org/10.1021/ja00314a003 . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Klassen, Anderson, et al., 1996
Klassen, J.S.; Anderson, S.G.; Blades, A.T.; Kebarle, P., Reaction Enthalpies for M+L = M+ + L, Where M+ = Na+ and K+ and L = Acetamide, N-Methylacetamide, N,N-Dimethylacetamide, Glycine, and Glycylglycine, from Determinations of the Collision-Induced Dissociation Thresholds, J. Phys. Chem., 1996, 100, 33, 14218, https://doi.org/10.1021/jp9608382 . [all data]

Sunner, 1984
Sunner, J. Kebarle, Ion - Solvent Molecule Interactions in the Gas Phase. The Potassium Ion and Me2SO, DMA, DMF, and Acetone, J. Am. Chem. Soc., 1984, 106, 21, 6135, https://doi.org/10.1021/ja00333a002 . [all data]

Beak, Lee, et al., 1978
Beak, P.; Lee, J.-K.; Zeigler, J.M., Equilibration studies: amide-imidate and thioamide-thioimidate functions, J. Org. Chem., 1978, 43, 1536-1538. [all data]


Notes

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