Formamide, N,N-dimethyl-

• Formula: C₃H₇NO
• Molecular weight: 73.0938
• IUPAC Standard InChI: InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3 Copy

  
• IUPAC Standard InChIKey: ZMXDDKWLCZADIW-UHFFFAOYSA-N Copy
• CAS Registry Number: 68-12-2
• 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: Dimethylformamide; DMF; DMF (amide); DMFA; N-Formyldimethylamine; N,N-Dimethylformamide; HCON(CH3)2; Formyldimethylamine; Dimethylforamide; Dimethylformamid; Dimetilformamide; Dwumetyloformamid; N,N-Dimethylmethanamide; NSC-5356; U-4224; Dimethylamid kyseliny mravenci; Dimetylformamidu; NCI-C60913; UN 2265; DMF (dimethylformamide); N,N-Dimethylformaldehyde
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible spectrum
  • 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

Phase change data

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
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
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 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 C₃H₇NO⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₃H₆NO^- +  =

By formula: C₃H₆NO^- + H⁺ = C₃H₇NO

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

References

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

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]

Medard and Thomas, 1957
Medard, L.; Thomas, M., Chaleur de combustion de onze substances explosives ou apparentees a des explosifs, Mem. Poudres, 1957, 39, 195-208. [all data]

Grolier, Roux-Desgranges, et al., 1993
Grolier, J.-P.E.; Roux-Desgranges, G.; Berkane, M.; Jimenez, E.; Wilhelm, E., Heat capacities and densities of mixtures of very polar substances 2. Mixtures containing N,N-dimethylformamide, J. Chem. Thermodynam., 1993, 25(1), 41-50. [all data]

Kolker, Kulikov, et al., 1992
Kolker, A.M.; Kulikov, M.V.; Krestov, Al.G., Volumes and heat capacities of binary non-aqueous mixtures. Part 2. The systems acetonitrile-N,N-dimethylformamide and acetonitrile-hexamethylphosphoric triamide, Thermochim. Acta, 1992, 211, 73-84. [all data]

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]

Petrov, Peshekhodov, et al., 1989
Petrov, A.N.; Peshekhodov, P.B.; Al'per, G.A., Heat capacity of non-aqueous solutions of non-electrolyts with N,N-dimethylformamide as a base, Sbornik Nauch. Trud., Termodin. Rast. neelect., Ivanovo, Inst. nevod. rast., 1989, Akad. [all data]

Zegers and Somsen, 1984
Zegers, H.C.; Somsen, G., Partial molar volumes and heat capacities in (dimethylformamide + an n-alkanol), J. Chem. Thermodynam., 1984, 16, 225-235. [all data]

Vorob'ev and Yakovlev, 1982
Vorob'ev, A.F.; Yakovlev, P.N., The specific heats of dimethylformamide-water and hexamethylphosphoramide-water mixtures, Zhur. Fiz. Khim., 1982, 56, 1933-1936. [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]

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De Visser, Perron, et al., 1977
De Visser, C.; Perron, G.; Desnoyers, J.E., Volumes and heat capacities of ternary aqueous systems at 25°C. Mixtures of urea, tert-butyl alcohol, N,N-dimethylformamide, and water, J. Amer. Chem. Soc., 1977, 99, 5894-5900. [all data]

De Visser, Perron, et al., 1977, 2
De Visser, C.; Perron, G.; Desnoyers, J.E.; Heuvelsland, W.J.M.; Somsen, G., Volumes and heat capacities of mixtures of N,N-dimethylformamide and water at 298.15 K, J. Chem. Eng. Data, 1977, 22, 74-79. [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]

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]

Geller, 1961
Geller, B.E., Some physicochemical properties of dimethylformamide, Zhur. Fiz. Khim., 1961, 35, 2210-2216. [all data]

Dreisbach, 1955
Dreisbach, R.R., Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]

Teja and Anselme, 1990
Teja, A.S.; Anselme, M.J., The critical properties of thermally stable and unstable fluids. I. 1985 results, AIChE Symp. Ser., 1990, 86, 279, 115-21. [all data]

Panneerselvam, Antony, et al., 2009
Panneerselvam, K.; Antony, M.P.; Srinivasan, T.G.; Vasudeva Rao, P.R., Enthalpies of vaporization of N,N-dialkyl monamides at 298.15K, Thermochimica Acta, 2009, 495, 1-2, 1-4, https://doi.org/10.1016/j.tca.2009.05.007 . [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
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Geller, 1961, 2
Geller, B.E., Properties of the dimethylformamide water system. I. Thermochemical properties, Russ. J. Phys. Chem. (Engl. Transl.), 1961, 35, 542-564. [all data]

Muñoz, Montón, et al., 2005
Muñoz, R.; Montón, J.B.; Burguet, M.C.; de la Torre, J., Phase equilibria in the systems isobutyl alcohol+N,N-dimethylformamide, isobutyl acetate+N,N-dimethylformamide and isobutyl alcohol+isobutyl acetate+N,N-dimethylformamide at 101.3kPa, Fluid Phase Equilibria, 2005, 232, 1-2, 62-69, https://doi.org/10.1016/j.fluid.2005.03.014 . [all data]

Blanco, Beltrán, et al., 1997
Blanco, Beatriz; Beltrán, Sagrario; Cabezas, José Luis; Coca, José, Phase Equilibria of Binary Systems Formed by Hydrocarbons from Petroleum Fractions and the Solvents N -Methylpyrrolidone and N , N -Dimethylformamide. 1. Isobaric Vapor-Liquid Equilibria, J. Chem. Eng. Data, 1997, 42, 5, 938-942, https://doi.org/10.1021/je970059u . [all data]

Marzal, Gabaldon, et al., 1995
Marzal, Paula; Gabaldon, Carmen; Seco, Aurora; Monton, Juan B., Isobaric Vapor-Liquid Equilibria of 1-Butanol + N,N-Dimethylformamide and 1-Pentanol + N,N-Dimethylformamide Systems at 50.00 and 100.00 kPa, J. Chem. Eng. Data, 1995, 40, 3, 589-592, https://doi.org/10.1021/je00019a010 . [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]

Bludilina, Baev, et al., 1979
Bludilina, V.I.; Baev, A.K.; Matveev, V.K.; Gaidym, I.L.; Shcherbina, E.I., Zh. Fiz. Khim., 1979, 53, 1052. [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]

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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]

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Karyakin, N.V.; Rabinovich, I.B.; Pal'tseva, N.G., Thermodynamics of the reactions of aromatic diamines with dianhydrides of tetracarboxylic acids, Vysokomol. Soedin, Ser., 1978, A 20(9), 2025-2029. [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]

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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]

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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]

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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]

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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]

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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]

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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]

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DePuy, C.H.; Grabowski, J.J.; Bierbaum, V.M.; Ingemann, S.; Nibbering, N.M.M., Gas-phase reactions of anions with methyl formate and N,N-dimethylformamide, J. Am. Chem. Soc., 1985, 107, 1093. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid 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
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

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