Acetamide, N-methyl-

• Formula: C₃H₇NO
• Molecular weight: 73.0938
• IUPAC Standard InChI: InChI=1S/C3H7NO/c1-3(5)4-2/h1-2H3,(H,4,5) Copy

  
• IUPAC Standard InChIKey: OHLUUHNLEMFGTQ-UHFFFAOYSA-N Copy
• CAS Registry Number: 79-16-3
• 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: Methylacetamide; Monomethylacetamide; N-Methylacetamide; CH3CONHCH3; Acetylmethylamine; N-Acetyl-N-methylamine; X 44
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry 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
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Condensed phase thermochemistry data

Go To: Top, Phase change data, Gas phase ion energetics data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change data

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Antoine Equation Parameters

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change 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

View reactions leading to C₃H₇NO⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₃H₆NO^- +  =

By formula: C₃H₆NO^- + H⁺ = C₃H₇NO

References

Go To: Top, Condensed phase thermochemistry data, Phase change 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.

Vasil'eva and Zhil'tsova, 1982
Vasil'eva, T.F.; Zhil'tsova, E.N., Heat of combustion of two monomethylamides, Termodin. Organ. Soedin., 1982, 108-110. [all data]

Roux, Jimenez, et al., 1996
Roux, M.V.; Jimenez, P.; Davalos, J.Z.; Castano, O.; Molina, M.T.; Notario, R.; Herreros, M.; Abboud, J.-L.M., The first direct experimental determination of strain in neutral and protonated 2-azetidinone, J. Am. Chem. Soc., 1996, 118, 12735-12737. [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]

Casteel and Amis, 1974
Casteel, J.F.; Amis, E.S., Conductance of Sodium Perchlorate in Water-N-Methylacetamide (NMA) Solvent System, J. Chem. Eng. Data, 1974, 19, 121. [all data]

Boje and Hvidt, 1971
Boje, L.; Hvidt, A., Densities of aqueous mixtures of non-electrolytes, J. Chem. Thermodyn., 1971, 3, 663. [all data]

Bonner and Kim, 1970
Bonner, O.D.; Kim, S.J., Intermolecular Association in Structured Liquids 1. Ethylene Carbonate and N-Methylacetamide, J. Chem. Thermodyn., 1970, 2, 63. [all data]

Starzewski, Wadso, et al., 1984
Starzewski, P.; Wadso, I.; Zielenkiewicz, W., Enthalpies of vaporization of some N-alkylamides at 298.15 K, J. Chem. Thermodyn., 1984, 16, 331-334. [all data]

Schmelzer and Pusch, 1995
Schmelzer, Jürgen; Pusch, Jens, Phase equilibria in binary systems containing N-monosubstituted amides and hydrocarbons, Fluid Phase Equilibria, 1995, 110, 1-2, 183-196, https://doi.org/10.1016/0378-3812(95)02753-2 . [all data]

Aucejo, Monton, et al., 1993
Aucejo, Antonio; Monton, Juan B.; Munoz, Rosa; Sanchotello, Margarita, Isobaric vapor-liquid equilibrium data for the cyclohexanone + N-methylacetamide system, J. Chem. Eng. Data, 1993, 38, 1, 160-162, https://doi.org/10.1021/je00009a039 . [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., 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]

Aihara, 1952
Aihara, A., J. Chem. Soc. Jpn. Pure Chem. Sect., 1952, 73, 855. [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [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]

Kreis and Wood, 1969
Kreis, R.W.; Wood, R.H., Enthalpy of fusion and cryoscopic constant of N-methylacetamide, The Journal of Chemical Thermodynamics, 1969, 1, 6, 523-526, https://doi.org/10.1016/0021-9614(69)90012-3 . [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]

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]

Decouzon, Exner, et al., 1990
Decouzon, M.; Exner, O.; Gal, J.-F.; Maria, P.-C., The Gas-Phase Acidity and the Acidic Site of Acetohydroxamic Acid: an FT-ICR Study, J. Org. Chem., 1990, 55, 13, 3980, https://doi.org/10.1021/jo00300a007 . [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.