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, Gas Chromatography, 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 | 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, Phase change data, Gas Chromatography, 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 |
Gas Chromatography
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
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CBP-1 | 752. | Shimadzu, 2003 | 25. m/0.2 mm/0.25 μm, He, 50. C @ 5. min, 4. K/min; Tend: 200. C |
Kovats' RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CBP-20 | 1333. | Shimadzu, 2003 | 25. m/0.2 mm/0.25 μm, He, 50. C @ 5. min, 4. K/min; Tend: 200. C |
Capillary | Carbowax 20M | 1304. | Nishimura, Yamaguchi, et al., 1989 | 2. K/min; Column length: 50. m; Column diameter: 0.22 mm; Tstart: 80. C; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SPB-Sulfur | 756.3 | de Lacy Costello, Evans, et al., 2001 | 30. m/0.32 mm/4. μm, 40. C @ 12.5 min, 4. K/min; Tend: 200. C |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 1326. | Chung, Yung, et al., 2002 | 60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min |
Capillary | Supelcowax-10 | 1326. | Chung, Yung, et al., 2001 | 60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min |
Capillary | Supelcowax-10 | 1328. | Chung and Cadwallader, 1993 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 195. C @ 40. min |
Capillary | DB-Wax | 1319. | Umano, Hagi, et al., 1992 | He, 40. C @ 10. min, 2. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 200. C |
Capillary | DB-Wax | 1282. | Frohlich and Schreier, 1990 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 3. min, 5. K/min; Tend: 220. C |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Methyl Silicone | 100. | 747. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 120. | 750. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 140. | 753. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 80. | 745. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | DB-1 | 60. | 742. | Shimadzu, 2003, 2 | 60. m/0.32 mm/1. μm, He |
Packed | DC-400 | 150. | 790. | Anderson, 1968 | Helium, Gas-Pak (60-80 mesh); Column length: 3.0 m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 772. | Radulovic, Blagojevic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
Capillary | VF-5 | 783. | Li and Zhao, 2009 | 30. m/0.25 mm/0.25 μm, Helium, 60. C @ 2. min, 10. K/min, 300. C @ 10. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SPB-1 | 746. | Flanagan, Streete, et al., 1997 | 60. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C |
Capillary | Methyl Silicone | 751. | Zenkevich, Korolenko, et al., 1995 | Program: not specified |
Capillary | SPB-1 | 746. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C |
Capillary | DB-1 | 735. | Kawai, Ishida, et al., 1991 | 60. m/0.25 mm/0.25 μm; Program: not specified |
Capillary | DB-1 | 738. | Kawai, Ishida, et al., 1991 | 60. m/0.25 mm/0.25 μm; Program: not specified |
Capillary | CP Sil 8 CB | 782. | Weller and Wolf, 1989 | 40. m/0.25 mm/0.25 μm, He; Program: 30 0C (1 min) 15 0C/min -> 45 0C 3 0C/min -> 120 0C |
Normal alkane RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | DB-Wax | 60. | 1344. | Shimadzu, 2003, 2 | 50. m/0.32 mm/1. μm, He |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1361. | Shimadzu, 2012 | 30. m/0.32 mm/0.50 μm, Helium, 4. K/min; Tstart: 40. C; Tend: 260. C |
Capillary | DB-Wax | 1361. | Shimadzu Corporation, 2003 | 30. m/0.32 mm/0.5 μm, He, 4. K/min; Tstart: 40. C; Tend: 260. C |
Capillary | PEG-20M | 1295. | Kubota, Matsujage, et al., 1996 | 50. m/0.25 mm/0.25 μm, Nitrogen, 2. K/min; Tstart: 60. C; Tend: 180. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polyethylene Glycol | 1325. | Zenkevich, Korolenko, et al., 1995 | Program: not specified |
Capillary | DB-Wax | 1312. | Peng, Yang, et al., 1991 | Program: not specified |
Capillary | DB-Wax | 1327. | Peng, Yang, et al., 1991 | Program: not specified |
Capillary | CP-Wax 52CB | 1290. | Vernin, 1991 | Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | Superox 0.6; Carbowax 20M | 1276. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc. | 1276. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, 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]
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Enthalpies of vaporization of N,N-dialkyl monamides at 298.15K,
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Properties of the dimethylformamide water system. I. Thermochemical properties,
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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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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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Vapour Pressures of Some Mono- and Di-Alkyl Substituted Aliphatic Amides at Different Temperatures,
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Volatile Constituents of Loquat (Eriobotrya japonica Lindl.) Fruit,
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Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, 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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