Formamide, N,N-dimethyl-
Formula: C3H7NO
IUPAC Standard InChI: InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
IUPAC Standard InChIKey: ZMXDDKWLCZADIW-UHFFFAOYSA-N
CAS Registry Number: 68-12-2
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
Condensed phase thermochemistry data
Ion clustering data
IR Spectrum
Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
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Individual Reactions
C7H7NO3- + = (C7H7NO3- • )
By formula: C7H7NO3- + C3H7NO = (C7H7NO3- • C3H7NO)
ΔrG° 25. ± 6.7 kJ/mol IMRE Chowdhury, Grimsrud, et al., 1987 gas phase; Free energy affinity at 70°C.; B
Free energy of reaction
ΔrG° (kJ/mol)
25. 343. PHPMS Chowdhury, 1987 gas phase; M
C7H4N2O2- + = (C7H4N2O2- • )
By formula: C7H4N2O2- + C3H7NO = (C7H4N2O2- • C3H7NO)
C6H4FNO2- + = (C6H4FNO2- • )
By formula: C6H4FNO2- + C3H7NO = (C6H4FNO2- • C3H7NO)
C6F4O2- + = (C6F4O2- • )
By formula: C6F4O2- + C3H7NO = (C6F4O2- • C3H7NO)
+ = ( • )
By formula: C6H4O2- + C3H7NO = (C6H4O2- • C3H7NO)
By formula: K+ + C3H7NO = (K+ • C3H7NO)
ΔrH° 123. kJ/mol CIDT Klassen, Anderson, et al., 1996 RCD
ΔrH° 130. kJ/mol HPMS Sunner, 1984 gas phase; M
ΔrS° 110. J/mol*K HPMS Sunner, 1984 gas phase; M
C7H4F3NO2- + = (C7H4F3NO2- • )
By formula: C7H4F3NO2- + C3H7NO = (C7H4F3NO2- • C3H7NO)
By formula: Na+ + C3H7NO = (Na+ • C3H7NO)
ΔrH° 156. ± 4. kJ/mol CIDT Armentrout and Rodgers, 2000 See 96KLA/AND?; RCD
126. 298. IMRE McMahon and Ohanessian, 2000 Anchor alanine=39.89; RCD
C3H6NO- + =
By formula: C3H6NO- + H+ = C3H7NO
ΔrH° 1670. ± 17. kJ/mol G+TS DePuy, Grabowski, et al., 1985 gas phase; B
ΔrG° 1640. ± 17. kJ/mol IMRB DePuy, Grabowski, et al., 1985 gas phase; B
By formula: Li+ + C3H7NO = (Li+ • C3H7NO)
ΔrH° 210. kJ/mol ICR Staley and Beauchamp, 1975 gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M
( • 2 ) + = ( • 3 )
By formula: (K+ • 2C3H7NO) + C3H7NO = (K+ • 3C3H7NO)
ΔrH° 63. kJ/mol HPMS Sunner, 1984 gas phase; M
ΔrS° 75. J/mol*K HPMS Sunner, 1984 gas phase; M
( • ) + = ( • 2 )
By formula: (K+ • C3H7NO) + C3H7NO = (K+ • 2C3H7NO)
Go To: Top, Reaction thermochemistry data, Notes
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]
Go To: Top, Reaction thermochemistry data, References
T Temperature
ΔrG° Free energy of reaction at standard conditions
ΔrH° Enthalpy of reaction at standard conditions
ΔrS° Entropy of reaction at standard conditions