Formamide, N-methyl-

• Formula: C₂H₅NO
• Molecular weight: 59.0672
• IUPAC Standard InChI: InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4) Copy

  
• IUPAC Standard InChIKey: ATHHXGZTWNVVOU-UHFFFAOYSA-N Copy
• CAS Registry Number: 123-39-7
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Methylformamide; Monomethylformamide; N-Methylformamide; HCONHCH3; EK 7011; NSC 3051; X 188; N-Monomethylformamide
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • Ion clustering data
• 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 by: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - 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

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₂H₄NO^- +  =

By formula: C₂H₄NO^- + H⁺ = C₂H₅NO

IR Spectrum

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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

Gas Phase Spectrum

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Additional Data

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

UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

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

Kulikov, Krestov, et al., 1989
Kulikov, M.V.; Krestov, A.G.; Safonova, L.P.; Kolker, A.M., Excess thermodynamic functions in the systems water + N-methylformamide, and water + N,N-dimethylformamide, Sbornik Nauch Trud., Termodin. rast. neelect., Ivanovo, Inst. nevod. rast., 1989, Akad. [all data]

de Visser and Somsen, 1979
de Visser, C.; Somsen, G., Thermochemical behavior of mixtures of N,N-dimethylformamide with dimethylsulfoxide, acetonitrile, and N-methylformamide: volumes and heat capacities, J. Solution Chem., 1979, 8, 593-600. [all data]

Bonner and Cerutti, 1976
Bonner, O.D.; Cerutti, P.J., The partial molar heat capacities of some solutes in water and deuterium oxide, J. Chem. Thermodynam., 1976, 8, 105-111. [all data]

Skold, Suurkuusk, et al., 1976
Skold, R.; Suurkuusk, J.; Wadso, I., Thermochemistry of solutions of biochemical model compounds. 7. Aqueous solutions of some amides, t-butanol, and pentanol, J. Chem. Thermodynam., 1976, 8, 1075-1080. [all data]

de Visser and Somsen, 1974
de Visser, C.; Somsen, G., Molar heat capacities of binary mixtures of water and some amides at 298.15 K, Z. Physik. Chem. [N.F.], 1974, 92, 159-162. [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]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Ushakov, Sedov, et al., 1996
Ushakov, V.S.; Sedov, S.M.; Knyazev, B.A.; Kuchkaev, B.I., Thermodynamic properties of N-methylformamide, Zh. Fiz. Khim., 1996, 70, 9, 1573. [all data]

Barone, Castronuovo, et al., 1985
Barone, G.; Castronuovo, G.; Della Gatta, G.; Elia, V.; Iannone, A., Enthalpies of vaporization of seven alkylamides, Fluid Phase Equilibria, 1985, 21, 1-2, 157-164, https://doi.org/10.1016/0378-3812(85)90066-4 . [all data]

Varushchenko, 1986
Varushchenko, R.M., Zh. Fiz. Khim., 1986, 60, 291. [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]

Heinrich, Ilavsky, et al., 1961
Heinrich, J.; Ilavsky, J.; Surovy, J., Chem. Zvesti, 1961, 15, 414. [all data]

Dykyj, 1970
Dykyj, J., Petrochemica, 1970, 10, 2, 51. [all data]

Heinrich, Ilavsky, et al., 1961, 2
Heinrich, J.; Ilavsky, J.; Surovy, J., Dependence of the Vapor Pressure of N-Methylformamide from the Temperature Equilibrium Liquid-Vapor for the System N-Methyl-Formamide-Water, Chem. Zvesti, 1961, 15, 6, 414-418. [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]

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]

Desfrancois, Periquet, et al., 1999
Desfrancois, C.; Periquet, V.; Carles, S.; Schermann, J.P.; Smith, D.M.A.; Adamowicz, L., Experimental and ab initio theoretical studies of electron binding to formamide, N-methylformamide, and N,N-dimethylformamide., J. Chem. Phys., 1999, 110, 9, 4309-4314, https://doi.org/10.1063/1.478353 . [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [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]

Brundle, Turner, et al., 1969
Brundle, C.R.; Turner, D.W.; Robin, M.B.; Basch, H., Photoelectron spectroscopy of simple amides and carboxylic acids, Chem. Phys. Lett., 1969, 3, 292. [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]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Nielsen and Schellman, 1967
Nielsen, E.B.; Schellman, J.A., The absorption spectra of simple amides and peptides, J. Phys. Chem., 1967, 71, 7, 2297-2304. [all data]

Krawczyk and Piotrowski, 1989
Krawczyk, W.; Piotrowski, G.T., Relationships Between Structure and Retention Index for N-Substituted Amides of Aliphatic Acids on a Non-Polar Column, J. Chromatogr., 1989, 463, 297-304, https://doi.org/10.1016/S0021-9673(01)84484-8 . [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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