Formamide, N,N-dimethyl-
- Formula: C3H7NO
- Molecular weight: 73.0938
- IUPAC Standard InChIKey: ZMXDDKWLCZADIW-UHFFFAOYSA-N
- 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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Condensed phase thermochemistry data
Go To: Top, Phase change 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -57.21 ± 0.29 | kcal/mol | Ccb | Vasil'eva, Zhil'tsova, et al., 1972 | ALS |
ΔfH°liquid | -57.13 | kcal/mol | Ccb | Medard and Thomas, 1957 | Heat of combustion corrected for pressure; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -464.06 ± 0.29 | kcal/mol | Ccb | Vasil'eva, Zhil'tsova, et al., 1972 | ALS |
ΔcH°liquid | -464.13 | kcal/mol | Ccb | Medard and Thomas, 1957 | Heat of combustion corrected for pressure; ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
34.907 | 298.15 | Grolier, Roux-Desgranges, et al., 1993 | DH |
35.411 | 298.15 | Kolker, Kulikov, et al., 1992 | T = 283 to 323 K.; DH |
35.679 | 308. | Kulikov, Krestov, et al., 1989 | DH |
35.85 | 298.15 | Petrov, Peshekhodov, et al., 1989 | T = 258.15, 278.15, 298.15, 318.15 K.; DH |
35.459 | 298.15 | Zegers and Somsen, 1984 | DH |
35.97 | 298.15 | Vorob'ev and Yakovlev, 1982 | T = 297.15 to 299.15 K. Cp given as 2.059 J/g*K.; DH |
36.04 | 298.15 | de Visser and Somsen, 1979 | DH |
28.80 | 298. | Marchidan and Ciopec, 1978 | T = 298 to 427 K. Mean value over range.; DH |
35.4 | 298.15 | De Visser, Perron, et al., 1977 | DH |
35.4 | 298. | De Visser, Perron, et al., 1977 | One temperature only.; DH |
36.04 | 298.15 | De Visser, Perron, et al., 1977, 2 | DH |
34.9 | 298.15 | Bonner and Cerutti, 1976 | DH |
36.33 | 298.15 | de Visser and Somsen, 1974 | DH |
37.450 | 298. | Geller, 1961 | T = 273 to 323 K.; DH |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 426. ± 1. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 212.7 | K | N/A | Dreisbach, 1955 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 649.6 | K | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.82 | mol/l | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.08 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.2 ± 0.1 | kcal/mol | CGC | Panneerselvam, Antony, et al., 2009 | Based on data from 463. to 513. K.; AC |
ΔvapH° | 11.2 | kcal/mol | A | Barone, Castronuovo, et al., 1985 | See also Majer and Svoboda, 1985.; AC |
ΔvapH° | 11.37 | kcal/mol | E | Geller, 1961, 2 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.3 | 361. | N/A | Muñoz, Montón, et al., 2005 | Based on data from 346. to 425. K.; AC |
9.99 | 392. | N/A | Blanco, Beltrán, et al., 1997 | Based on data from 377. to 426. K.; AC |
10.4 | 353. | N/A | Marzal, Gabaldon, et al., 1995 | Based on data from 338. to 425. K.; AC |
11.8 | 316. | A | Stephenson and Malanowski, 1987 | Based on data from 301. to 426. K.; AC |
10.2 | 370. | N/A | Bludilina, Baev, et al., 1979 | Based on data from 318. to 423. K.; AC |
13.6 | 346. | N/A | Myasinkova, Schmelev, et al., 1974 | Based on data from 331. to 425. K. See also Boublik, Fried, et al., 1984.; AC |
11.2 | 318. | N/A | Gopal and Rizvi, 1968 | Based on data from 303. to 363. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
303. to 363. | 3.92497 | 1337.716 | -82.648 | Gopal and Rizvi, 1968, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
2.139 | 212.85 | N/A | Karyakin, Rabinovich, et al., 1978 | DH |
2.14 | 212.9 | AC | Smirnova, Tsvetkova, et al., 2007 | AC |
2.14 | 212.9 | N/A | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.99 | 212.85 | Karyakin, Rabinovich, et al., 1978 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.13 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 212.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 204.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Reference | Comment |
---|---|---|
0.01362 | Desfrancois, Periquet, et al., 1999 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.45 ± 0.05 | EI | Baldwin, Loudon, et al., 1977 | LLK |
9.14 | PE | Brundle, Turner, et al., 1969 | RDSH |
9.12 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.14 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
9.25 | PE | Henriksen, Isaksson, et al., 1981 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 14.50 | ? | EI | Loudon and Webb, 1977 | LLK |
CHO+ | 14.3 ± 0.1 | ? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
C2H6N+ | 11.60 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H6N+ | 11.6 ± 0.1 | ? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
C3H6NO+ | 11.35 | ? | EI | Loudon and Webb, 1977 | LLK |
De-protonation reactions
C3H6NO- + =
By formula: C3H6NO- + H+ = C3H7NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 399.1 ± 4.1 | kcal/mol | G+TS | DePuy, Grabowski, et al., 1985 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 392.0 ± 4.0 | kcal/mol | IMRB | DePuy, Grabowski, et al., 1985 | gas phase; B |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References, Notes
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
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118531 |
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
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Chaleur de combustion de onze substances explosives ou apparentees a des explosifs,
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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,
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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,
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Excess thermodynamic functions in the systems water + N-methylformamide, and water + N,N-dimethylformamide, Sbornik Nauch Trud., Termodin. rast. neelect., Ivanovo,
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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,
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Partial molar volumes and heat capacities in (dimethylformamide + an n-alkanol),
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Vorob'ev, A.F.; Yakovlev, P.N.,
The specific heats of dimethylformamide-water and hexamethylphosphoramide-water mixtures,
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de Visser, C.; Somsen, G.,
Thermochemical behavior of mixtures of N,N-dimethylformamide with dimethylsulfoxide, acetonitrile, and N-methylformamide: volumes and heat capacities,
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Relative enthalpies and related thermodynamic functions of some organic compounds by drop calorimetry,
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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,
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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,
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The partial molar heat capacities of some solutes in water and deuterium oxide,
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Some physicochemical properties of dimethylformamide,
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Geller, B.E.,
Properties of the dimethylformamide water system. I. Thermochemical properties,
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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,
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. [all data]
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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,
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. [all data]
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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,
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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, R.; Rizvi, S.A.,
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Gopal, R.; Rizvi, S.A.,
Vapour Pressures of Some Mono- and Di-Alkyl Substituted Aliphatic Amides at Different Temperatures,
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Thermodynamic properties of N,N-dimethylformamide and N,N-dimethylacetamide,
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Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
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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.,
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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,
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Ionization potentials of some molecules,
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30.4-nm He(II) photoelectron spectra of organic molecules,
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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,
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Gowenlock, B.G.; Jones, P.P.; Majer, J.R.,
Bond dissociation energies in some molecules containing alkyl substituted CH3, NH2, and OH,
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DePuy, C.H.; Grabowski, J.J.; Bierbaum, V.M.; Ingemann, S.; Nibbering, N.M.M.,
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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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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