N,N-Dimethylacetamide

• Formula: C₄H₉NO
• Molecular weight: 87.1204
• IUPAC Standard InChI: InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3 Copy

  
• IUPAC Standard InChIKey: FXHOOIRPVKKKFG-UHFFFAOYSA-N Copy
• CAS Registry Number: 127-19-5
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Acetamide, N,N-dimethyl-; Acetdimethylamide; Dimethylacetamide; Dimethylamide acetate; DMA; CH3CON(CH3)2; Acetic acid dimethylamide; Acetyl dimethylamine; CBC 510337; DMAc; Hallucinogen; N,N-Dimethylethanamide; NSC 3138; SK 7176; U-5954; Dimethylamid kyseliny octove
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• Information on this page:
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Constant pressure heat capacity of liquid

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, 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

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₈NO^- +  =

By formula: C₄H₈NO^- + H⁺ = C₄H₉NO

References

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, 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]

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]

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]

Notes

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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