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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₇H₇NO₃^- +  = (C₇H₇NO₃^- • )

By formula: C₇H₇NO₃^- + C₃H₇NO = (C₇H₇NO₃^- • C₃H₇NO)

Free energy of reaction

C₆H₅NO₂^- +  = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₃H₇NO = (C₆H₅NO₂^- • C₃H₇NO)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₃H₇NO = (C₇H₄N₂O₂^- • C₃H₇NO)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₃H₇NO = (C₆H₄FNO₂^- • C₃H₇NO)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₃H₇NO = (C₆H₄FNO₂^- • C₃H₇NO)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₃H₇NO = (C₆H₄FNO₂^- • C₃H₇NO)

Free energy of reaction

C₇H₇NO₃^- +  = (C₇H₇NO₃^- • )

By formula: C₇H₇NO₃^- + C₃H₇NO = (C₇H₇NO₃^- • C₃H₇NO)

Free energy of reaction

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₃H₇NO = (C₇H₇NO₂^- • C₃H₇NO)

Free energy of reaction

C₆H₄N₂O₄^- +  = (C₆H₄N₂O₄^- • )

By formula: C₆H₄N₂O₄^- + C₃H₇NO = (C₆H₄N₂O₄^- • C₃H₇NO)

Free energy of reaction

C₆H₄N₂O₄^- +  = (C₆H₄N₂O₄^- • )

By formula: C₆H₄N₂O₄^- + C₃H₇NO = (C₆H₄N₂O₄^- • C₃H₇NO)

Free energy of reaction

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₃H₇NO = (C₇H₇NO₂^- • C₃H₇NO)

Free energy of reaction

C₆F₄O₂^- +  = (C₆F₄O₂^- • )

By formula: C₆F₄O₂^- + C₃H₇NO = (C₆F₄O₂^- • C₃H₇NO)

Free energy of reaction

 +  = ( • )

By formula: C₆H₄O₂^- + C₃H₇NO = (C₆H₄O₂^- • C₃H₇NO)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₃H₇NO = (C₇H₄N₂O₂^- • C₃H₇NO)

Free energy of reaction

 +  = ( • )

By formula: K⁺ + C₃H₇NO = (K⁺ • C₃H₇NO)

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₃H₇NO = (C₇H₄N₂O₂^- • C₃H₇NO)

Free energy of reaction

C₇H₄F₃NO₂^- +  = (C₇H₄F₃NO₂^- • )

By formula: C₇H₄F₃NO₂^- + C₃H₇NO = (C₇H₄F₃NO₂^- • C₃H₇NO)

Free energy of reaction

 +  = ( • )

By formula: Na⁺ + C₃H₇NO = (Na⁺ • C₃H₇NO)

Free energy of reaction

C₃H₆NO^- +  =

By formula: C₃H₆NO^- + H⁺ = C₃H₇NO

 +  = ( • )

By formula: Li⁺ + C₃H₇NO = (Li⁺ • C₃H₇NO)

( • 2) +  = ( • 3)

By formula: (K⁺ • 2C₃H₇NO) + C₃H₇NO = (K⁺ • 3C₃H₇NO)

( • 3) +  = ( • 4)

By formula: (K⁺ • 3C₃H₇NO) + C₃H₇NO = (K⁺ • 4C₃H₇NO)

( • ) +  = ( • 2)

By formula: (K⁺ • C₃H₇NO) + C₃H₇NO = (K⁺ • 2C₃H₇NO)

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Ion clustering data, IR Spectrum, 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
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

Ion clustering data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₆F₄O₂^- +  = (C₆F₄O₂^- • )

By formula: C₆F₄O₂^- + C₃H₇NO = (C₆F₄O₂^- • C₃H₇NO)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₃H₇NO = (C₆H₄FNO₂^- • C₃H₇NO)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₃H₇NO = (C₆H₄FNO₂^- • C₃H₇NO)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₃H₇NO = (C₆H₄FNO₂^- • C₃H₇NO)

Free energy of reaction

C₆H₄N₂O₄^- +  = (C₆H₄N₂O₄^- • )

By formula: C₆H₄N₂O₄^- + C₃H₇NO = (C₆H₄N₂O₄^- • C₃H₇NO)

Free energy of reaction

C₆H₄N₂O₄^- +  = (C₆H₄N₂O₄^- • )

By formula: C₆H₄N₂O₄^- + C₃H₇NO = (C₆H₄N₂O₄^- • C₃H₇NO)

Free energy of reaction

 +  = ( • )

By formula: C₆H₄O₂^- + C₃H₇NO = (C₆H₄O₂^- • C₃H₇NO)

Free energy of reaction

C₆H₅NO₂^- +  = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₃H₇NO = (C₆H₅NO₂^- • C₃H₇NO)

Free energy of reaction

C₇H₄F₃NO₂^- +  = (C₇H₄F₃NO₂^- • )

By formula: C₇H₄F₃NO₂^- + C₃H₇NO = (C₇H₄F₃NO₂^- • C₃H₇NO)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₃H₇NO = (C₇H₄N₂O₂^- • C₃H₇NO)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₃H₇NO = (C₇H₄N₂O₂^- • C₃H₇NO)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₃H₇NO = (C₇H₄N₂O₂^- • C₃H₇NO)

Free energy of reaction

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₃H₇NO = (C₇H₇NO₂^- • C₃H₇NO)

Free energy of reaction

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₃H₇NO = (C₇H₇NO₂^- • C₃H₇NO)

Free energy of reaction

C₇H₇NO₃^- +  = (C₇H₇NO₃^- • )

By formula: C₇H₇NO₃^- + C₃H₇NO = (C₇H₇NO₃^- • C₃H₇NO)

Free energy of reaction

C₇H₇NO₃^- +  = (C₇H₇NO₃^- • )

By formula: C₇H₇NO₃^- + C₃H₇NO = (C₇H₇NO₃^- • C₃H₇NO)

Free energy of reaction

 +  = ( • )

By formula: K⁺ + C₃H₇NO = (K⁺ • C₃H₇NO)

( • ) +  = ( • 2)

By formula: (K⁺ • C₃H₇NO) + C₃H₇NO = (K⁺ • 2C₃H₇NO)

( • 2) +  = ( • 3)

By formula: (K⁺ • 2C₃H₇NO) + C₃H₇NO = (K⁺ • 3C₃H₇NO)

( • 3) +  = ( • 4)

By formula: (K⁺ • 3C₃H₇NO) + C₃H₇NO = (K⁺ • 4C₃H₇NO)

 +  = ( • )

By formula: Li⁺ + C₃H₇NO = (Li⁺ • C₃H₇NO)

 +  = ( • )

By formula: Na⁺ + C₃H₇NO = (Na⁺ • C₃H₇NO)

Free energy of reaction

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• GAS (10 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm^-1 resolution
• LIQUID (NEAT); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Notes

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

Chowdhury, Grimsrud, et al., 1987
Chowdhury, S.; Grimsrud, E.P.; Kebarle, P., Bonding of Charged Delocalized Anions to Protic and Dipolar Aprotic Solvent Molecules, J. Phys. Chem., 1987, 91, 10, 2551, https://doi.org/10.1021/j100294a021 . [all data]

Chowdhury, 1987
Chowdhury, S. Grimsrud, Bonding of Charge Delocalized Anions to Protic and Dipolar Aprotic Solvents, J. Phys. Chem., 1987, 91, 10, 2551, https://doi.org/10.1021/j100294a021 . [all data]

Klassen, Anderson, et al., 1996
Klassen, J.S.; Anderson, S.G.; Blades, A.T.; Kebarle, P., Reaction Enthalpies for M+L = M+ + L, Where M+ = Na+ and K+ and L = Acetamide, N-Methylacetamide, N,N-Dimethylacetamide, Glycine, and Glycylglycine, from Determinations of the Collision-Induced Dissociation Thresholds, J. Phys. Chem., 1996, 100, 33, 14218, https://doi.org/10.1021/jp9608382 . [all data]

Sunner, 1984
Sunner, J. Kebarle, Ion - Solvent Molecule Interactions in the Gas Phase. The Potassium Ion and Me2SO, DMA, DMF, and Acetone, J. Am. Chem. Soc., 1984, 106, 21, 6135, https://doi.org/10.1021/ja00333a002 . [all data]

Armentrout and Rodgers, 2000
Armentrout, P.B.; Rodgers, M.T., An Absolute Sodium Cation Affinity Scale: Threshold Collision-Induced Dissociation Experiments and ab Initio Theory, J. Phys. Chem A, 2000, 104, 11, 2238, https://doi.org/10.1021/jp991716n . [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

DePuy, Grabowski, et al., 1985
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]

Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [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]

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]

Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [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]

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]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• 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.
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