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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Phase change data
Go To: Top, 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° | 46.7 ± 0.5 | kJ/mol | CGC | Panneerselvam, Antony, et al., 2009 | Based on data from 463. to 513. K.; AC |
ΔvapH° | 46.9 | kJ/mol | A | Barone, Castronuovo, et al., 1985 | See also Majer and Svoboda, 1985.; AC |
ΔvapH° | 47.57 | kJ/mol | E | Geller, 1961 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
43.1 | 361. | N/A | Muñoz, Montón, et al., 2005 | Based on data from 346. to 425. K.; AC |
41.8 | 392. | N/A | Blanco, Beltrán, et al., 1997 | Based on data from 377. to 426. K.; AC |
43.6 | 353. | N/A | Marzal, Gabaldon, et al., 1995 | Based on data from 338. to 425. K.; AC |
49.2 | 316. | A | Stephenson and Malanowski, 1987 | Based on data from 301. to 426. K.; AC |
42.5 | 370. | N/A | Bludilina, Baev, et al., 1979 | Based on data from 318. to 423. K.; AC |
56.7 | 346. | N/A | Myasinkova, Schmelev, et al., 1974 | Based on data from 331. to 425. K. See also Boublik, Fried, et al., 1984.; AC |
46.7 | 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 (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
303. to 363. | 3.93068 | 1337.716 | -82.648 | Gopal and Rizvi, 1968, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.950 | 212.85 | N/A | Karyakin, Rabinovich, et al., 1978 | DH |
8.95 | 212.9 | AC | Smirnova, Tsvetkova, et al., 2007 | AC |
8.95 | 212.9 | N/A | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.8 | 212.85 | Karyakin, Rabinovich, et al., 1978 | DH |
Gas phase ion energetics data
Go To: Top, 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) | 887.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 856.6 | kJ/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° | 1670. ± 17. | kJ/mol | G+TS | DePuy, Grabowski, et al., 1985 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1640. ± 17. | kJ/mol | IMRB | DePuy, Grabowski, et al., 1985 | gas phase; B |
Mass spectrum (electron ionization)
Go To: Top, 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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Due to licensing restrictions, this spectrum cannot be downloaded.
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, 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.
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
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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
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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
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]
Gopal and Rizvi, 1968
Gopal, R.; Rizvi, S.A.,
J. Indian Chem. Soc., 1968, 45, 1, 13. [all data]
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]
Karyakin, Rabinovich, et al., 1978
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]
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]
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,
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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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point 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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