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N,N-Dimethylacetamide

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Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-71.72kcal/molCmGuthrie, 1974Heat of hydrolysis; ALS
Deltafliquid-71.28kcal/molCcbBaroody and Carpenter, 1972ALS
Deltafliquid-66.52 ± 0.36kcal/molCcbVasil'eva, Zhil'tsova, et al., 1972ALS
Quantity Value Units Method Reference Comment
Deltacliquid-617.11 ± 0.36kcal/molCcbVasil'eva, Zhil'tsova, et al., 1972ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
42.59298.15De Visser, Heuvelsland, et al., 1978DH

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil438.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Deltavap12. ± 2.kcal/molAVGN/AAverage of 7 values; Individual data points

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
10.8386.AStephenson and Malanowski, 1987Based on data from 371. - 423. K.; AC
10.8318.AStephenson and Malanowski, 1987Based on data from 303. - 363. K. See also Gopal and Rizvi, 1968.; AC
16.2312.N/AMyasinkova, Schmelev, et al., 1974Based on data from 297. - 438. K. See also Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
303. - 363.6.088802725.9628.209Gopal and Rizvi, 1968, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
2.44254.2Smirnova, Tsvetkova, et al., 2007AC
2.0253.2Lisicki and Jamróz, 2000AC
2.490251.4Ahlers, Lohmann, et al., 1999AC

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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

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
Deltar27.2kcal/molPHPMSMeot-Ner, 1984gas phase; M
Deltar27.2kcal/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Deltar24.1cal/mol*KPHPMSMeot-Ner, 1984gas phase; M
Deltar24.1cal/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

C4H8NO- + Hydrogen cation = N,N-Dimethylacetamide

By formula: C4H8NO- + H+ = C4H9NO

Quantity Value Units Method Reference Comment
Deltar374.8 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar368.1 ± 2.0kcal/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
Deltar31.3kcal/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Deltar27.4cal/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
Deltar29.0kcal/molCIDTKlassen, Anderson, et al., 1996RCD
Deltar31.kcal/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar23.cal/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
Deltar18.kcal/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar24.cal/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
Deltar24.kcal/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar24.cal/mol*KHPMSSunner, 1984gas phase; M

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

By formula: C4H9NO = C4H9NO

Quantity Value Units Method Reference Comment
Deltar16.1 ± 0.7kcal/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
Deltar37.5kcal/molCIDTKlassen, Anderson, et al., 1996RCD

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291288

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes

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

Guthrie, 1974
Guthrie, J.P., Hydration of carboxamides. Evaluation of the free energy change for addition of water to acetamide and formamide derivatives, J. Am. Chem. Soc., 1974, 96, 3608-3615. [all data]

Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A., Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [all data]

Vasil'eva, Zhil'tsova, et al., 1972
Vasil'eva, T.F.; Zhil'tsova, E.N.; Vvedenskii, A.A., Enthalpies of combustion of NN-dimethylformamide and NN-dimethylacetamide, Russ. J. Phys. Chem. (Engl. Transl.), 1972, 46, 315. [all data]

De Visser, Heuvelsland, et al., 1978
De Visser, C.; Heuvelsland, W.J.M.; Dunn, L.A.; Somsen, G., Some properties of binary aqueous liquid mixtures, J. Chem. Soc., Faraday Trans.1, 1978, 74, 1159-1169. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Gopal and Rizvi, 1968
Gopal, R.; Rizvi, S.A., J. Indian Chem. Soc., 1968, 45, 1, 13. [all data]

Myasinkova, Schmelev, et al., 1974
Myasinkova, L.F.; Schmelev, V.A.; Vaisman, I.L.; Bushinskii, V.I.; Novokhatka, D.A., Zh. Prikl. Khim. (Leningrad), 1974, 47, 2604. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Gopal and Rizvi, 1968, 2
Gopal, R.; Rizvi, S.A., Vapour Pressures of Some Mono- and Di-Alkyl Substituted Aliphatic Amides at Different Temperatures, J. Indian Chem. Soc., 1968, 45, 1, 13-16. [all data]

Smirnova, Tsvetkova, et al., 2007
Smirnova, N.N.; Tsvetkova, L.Ya.; Bykova, T.A.; Marcus, Yizhak, Thermodynamic properties of N,N-dimethylformamide and N,N-dimethylacetamide, The Journal of Chemical Thermodynamics, 2007, 39, 11, 1508-1513, https://doi.org/10.1016/j.jct.2007.02.009 . [all data]

Lisicki and Jamróz, 2000
Lisicki, Zygmunt; Jamróz, Malgorzata E., (Solid + liquid) equilibria in (polynuclear aromatic+ tertiary amide) systems, The Journal of Chemical Thermodynamics, 2000, 32, 10, 1335-1353, https://doi.org/10.1006/jcht.2000.0685 . [all data]

Ahlers, Lohmann, et al., 1999
Ahlers, Jens; Lohmann, Jürgen; Gmehling, Jürgen, Binary Solid-Liquid Equilibria of Organic Systems Containing Different Amides and Sulfolane, J. Chem. Eng. Data, 1999, 44, 4, 727-730, https://doi.org/10.1021/je9802975 . [all data]

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

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References