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
Δfliquid-300.1kJ/molCmGuthrie, 1974Heat of hydrolysis; ALS
Δfliquid-298.2kJ/molCcbBaroody and Carpenter, 1972ALS
Δfliquid-278.3 ± 1.5kJ/molCcbVasil'eva, Zhil'tsova, et al., 1972ALS
Quantity Value Units Method Reference Comment
Δcliquid-2582.0 ± 1.5kJ/molCcbVasil'eva, Zhil'tsova, et al., 1972ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
178.2298.15De 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
Δvap49. ± 7.kJ/molAVGN/AAverage of 7 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
45.1386.AStephenson and Malanowski, 1987Based on data from 371. to 423. K.; AC
45.2318.AStephenson and Malanowski, 1987Based on data from 303. to 363. K. See also Gopal and Rizvi, 1968.; AC
67.9312.N/AMyasinkova, Schmelev, et al., 1974Based on data from 297. to 438. K. See also Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
303. to 363.6.094512725.9628.209Gopal and Rizvi, 1968, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
10.2254.2Smirnova, Tsvetkova, et al., 2007AC
8.2253.2Lisicki and Jamróz, 2000AC
10.42251.4Ahlers, 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+ • N,N-Dimethylacetamide)

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

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

Quantity Value Units Method Reference Comment
Δr114.kJ/molPHPMSMeot-Ner, 1984gas phase; M
Δr114.kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr101.J/mol*KPHPMSMeot-Ner, 1984gas phase; M
Δr101.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
Δr1568. ± 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
Δr1540. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

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

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

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

Quantity Value Units Method Reference Comment
Δr131.kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr115.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

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

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

Quantity Value Units Method Reference Comment
Δr121.kJ/molCIDTKlassen, Anderson, et al., 1996RCD
Δr130.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KHPMSSunner, 1984gas phase; M

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

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

Quantity Value Units Method Reference Comment
Δr75.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KHPMSSunner, 1984gas phase; M

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

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

Quantity Value Units Method Reference Comment
Δr100.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr100.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
Δr67. ± 3.kJ/molEqkBeak, Lee, et al., 1978liquid phase; ALS

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

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

Quantity Value Units Method Reference Comment
Δr157.kJ/molCIDTKlassen, Anderson, et al., 1996RCD

Gas phase ion energetics data

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

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
Proton affinity (review)908.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity877.0kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.20 ± 0.05EIBaldwin, Loudon, et al., 1977LLK
8.81CTSSlifkin and Allison, 1967RDSH
8.81 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
9.43PESweigart and Turner, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+12.55?EILoudon and Webb, 1977LLK
C2H3O+11.4 ± 0.1?EIGowenlock, Jones, et al., 1961RDSH
C2H6N+12.15?EILoudon and Webb, 1977LLK
C2H6N+12.4 ± 0.1?EIGowenlock, Jones, et al., 1961RDSH
C3H6NO+11.60?EILoudon and Webb, 1977LLK

De-protonation reactions

C4H8NO- + Hydrogen cation = N,N-Dimethylacetamide

By formula: C4H8NO- + H+ = C4H9NO

Quantity Value Units Method Reference Comment
Δr1568. ± 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
Δr1540. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

Ion clustering data

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

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
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

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

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

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

Quantity Value Units Method Reference Comment
Δr114.kJ/molPHPMSMeot-Ner, 1984gas phase; M
Δr114.kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr101.J/mol*KPHPMSMeot-Ner, 1984gas phase; M
Δr101.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

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

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

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

Quantity Value Units Method Reference Comment
Δr131.kJ/molPHPMSMeot-Ner, 1984, 2gas phase; M
Quantity Value Units Method Reference Comment
Δr115.J/mol*KPHPMSMeot-Ner, 1984, 2gas phase; M

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

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

Quantity Value Units Method Reference Comment
Δr121.kJ/molCIDTKlassen, Anderson, et al., 1996RCD
Δr130.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KHPMSSunner, 1984gas phase; M

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

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

Quantity Value Units Method Reference Comment
Δr100.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KHPMSSunner, 1984gas phase; M

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

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

Quantity Value Units Method Reference Comment
Δr75.kJ/molHPMSSunner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KHPMSSunner, 1984gas phase; M

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

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

Quantity Value Units Method Reference Comment
Δr157.kJ/molCIDTKlassen, Anderson, et al., 1996RCD

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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)

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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 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, Gas phase ion energetics data, Ion clustering 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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Baldwin, Loudon, et al., 1977
Baldwin, M.A.; Loudon, A.G.; Webb, K.S.; Cardnell, P.C., Charge location and fragmentation under electron impact. V-The ionization potentials of (methylated) phosphoramides, guanidines, formamides, acetamides, ureas and thioureas, Org. Mass Spectrom., 1977, 12, 279. [all data]

Slifkin and Allison, 1967
Slifkin, M.A.; Allison, A.C., Measurement of ionization potentials from contact charge transfer spectra, Nature, 1967, 215, 949. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W., Lone pair orbitals and their interactions studied by photoelectron spectroscopy. I. Carboxylic acids and their derivatives, J. Am. Chem. Soc., 1972, 94, 5592. [all data]

Loudon and Webb, 1977
Loudon, A.G.; Webb, K.S., The nature of the [C2H6N]+ and [CH4N]+ ions formed by electron impact on methylated formamides, acetamides, ureas, thioureas and hexamethylphosphoramide, Org. Mass Spectrom., 1977, 12, 283. [all data]

Gowenlock, Jones, et al., 1961
Gowenlock, B.G.; Jones, P.P.; Majer, J.R., Bond dissociation energies in some molecules containing alkyl substituted CH3, NH2, and OH, J. Chem. Soc. Faraday Trans., 1961, 57, 23. [all data]


Notes

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