Formamide

• Formula: CH₃NO
• Molecular weight: 45.0406
• IUPAC Standard InChI: InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3) Copy

  
• IUPAC Standard InChIKey: ZHNUHDYFZUAESO-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-12-7
• 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: Carbamaldehyde; Methanamide; HCONH2; Amid kyseliny mravenci; Formimidic acid
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • 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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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Gas 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing

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 sublimation

Enthalpy of fusion

Entropy 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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 CH₃NO⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

CH₂NO^- +  =

By formula: CH₂NO^- + H⁺ = CH₃NO

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); BECKMAN IR-9 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

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

• gas

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

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

Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

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

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

Bauder and Gunthard, 1958
Bauder, A.; Gunthard, Hs.H., Thermodynamische Eigenschaften von Formamid, Helv. Chim. Acta, 1958, 41, 670-673. [all data]

DeWit, DeKruif, et al., 1983
DeWit, H.G.M.; DeKruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing organic crystals containing nitrogen, oxygen, and sulfur. II. Molar heat capacities of eight compounds by adiabatic calorimetry, J. Chem. Thermodynam., 1983, 15, 891-902. [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]

Vorob'ev, Privalova, et al., 1977
Vorob'ev, A.F.; Privalova, N.M.; Rekharskii, M.V., Hermetically sealed calorimeter with automatic adiabatic enclosure for determining the specific heats of liquids, Zhur. Fiz. Khim., 1977, 51, 1843-1846. [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]

Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A., Study of the heat capacity of selected solvents, Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]

Somsen and Coops, 1965
Somsen, G.; Coops, J., Enthalpies of solvation of alkali halides in formamide. I. The enthalpies of solution of alkali halides in formamide, Rec. Trav. chim., 1965, 84, 985-1002. [all data]

Timmermans and Hennaut-Roland, 1935
Timmermans, J.; Hennaut-Roland, M., Physical constants of 20 organic compounds. VII., J. Chim. Phys. Phys.-Chim. Biol., 1935, 32, 501. [all data]

Timmermans, 1935
Timmermans, J., Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds., Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]

Joukovsky, 1934
Joukovsky, N.I., Experimental Study of the Theory of Concentrated Solutions. XI. Thermodynamic Properties of Concentrated Solutions of Aliphatic Organic Compounds Containing Nitrogen., Bull. Soc. Chim. Belg., 1934, 43, 397. [all data]

De Wit, De Kruif, et al., 1983
De Wit, H.G.M.; De Kruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulfur II. Molar heat capacities of eight compounds by adiabatic calorimetry, J. Chem. Thermodyn., 1983, 15, 9, 891, https://doi.org/10.1016/0021-9614(83)90095-2 . [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]

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]

Majer and Svoboda, 1985, 2
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation, The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4 . [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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Daamen, van der Poel, et al., 1979
Daamen, H.; van der Poel, H.; Stufkens, D.J.; Oskam, A., The thermochemistry of M(CO)6-xLx (M = Cr, Mo, W; L = piperidine, pyridine, pyrazine, pyrazole, thiazole; x = 1, 2, 3), Thermochimica Acta, 1979, 34, 1, 69-83, https://doi.org/10.1016/0040-6031(79)80026-X . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

De Wit, De Kruif, et al., 1983, 2
De Wit, H.G.M.; De Kruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulfur II. Molar heat capacities of eight compounds by adiabatic calorimetry, The Journal of Chemical Thermodynamics, 1983, 15, 9, 891-902, https://doi.org/10.1016/0021-9614(83)90095-2 . [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]

Asbrink, Svensson, et al., 1981
Asbrink, L.; Svensson, A.; Von Niessen, W.; Bieri, G., 30.4 nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1981, 24, 293. [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]

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]

Vilesov, 1960
Vilesov, F.I., The photoionization of vapors of compounds whose molecules contain carbonyl groups, Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [all data]

Hunt and Simpson, 1953
Hunt, H.D.; Simpson, W.T., Spectra of simple amides in the vacuum ultraviolet, J. Am. Chem. Soc., 1953, 75, 4540. [all data]

Ballard, Jones, et al., 1987
Ballard, R.E.; Jones, J.; Read, D.; Inchley, A.; Cranmer, M., He(I) photoelectron studies of liquids and gases, Chem. Phys. Lett., 1987, 137, 125. [all data]

Henriksen, Isaksson, et al., 1981
Henriksen, L.; Isaksson, R.; Liljefors, T.; Sandstrom, J., Ultraviolet absorption and photoelectron spectra of some cyclic and open-chain mono- and dithiooxamides, Acta Chem. Scand., Ser. B, 1981, 35, 489. [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]

Prososki, Etzel, et al., 2007
Prososki, R.A.; Etzel, M.R.; Rankin, S.A., Solvent type affects the number, distribution, and relative quantities of volatile compounds found in sweet whey powder, J. Dairy Sci., 2007, 90, 2, 523-531, https://doi.org/10.3168/jds.S0022-0302(07)71535-7 . [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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy 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
  ΔvapH°	Enthalpy of vaporization at standard conditions

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