Formamide, N-methyl-
- Formula: C2H5NO
- Molecular weight: 59.0672
- IUPAC Standard InChIKey: ATHHXGZTWNVVOU-UHFFFAOYSA-N
- CAS Registry Number: 123-39-7
- 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: Methylformamide; Monomethylformamide; N-Methylformamide; HCONHCH3; EK 7011; NSC 3051; X 188; N-Monomethylformamide
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Phase change data
Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), 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:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 455.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 13.43 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 13.0 ± 0.31 | kcal/mol | N/A | Ushakov, Sedov, et al., 1996 | Based on data from 340. to 440. K.; AC |
ΔvapH° | 13.4 | kcal/mol | A | Barone, Castronuovo, et al., 1985 | See also Varushchenko, 1986.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.9 | 355. | N/A | Ushakov, Sedov, et al., 1996 | Based on data from 340. to 440. K.; AC |
13.0 | 325. | A | Stephenson and Malanowski, 1987 | Based on data from 310. to 391. K.; AC |
12.8 | 384. | A | Stephenson and Malanowski, 1987 | Based on data from 369. to 472. K. See also Heinrich, Ilavsky, et al., 1961 and Dykyj, 1970.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
369.6 to 472.4 | 4.99225 | 2134.031 | -45.071 | Heinrich, Ilavsky, et al., 1961, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.495 | 270.6 | Ahlers, Lohmann, et al., 1999 | AC |
Reaction thermochemistry data
Go To: Top, Phase change data, Mass spectrum (electron ionization), 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:
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
C2H4NO- + =
By formula: C2H4NO- + H+ = C2H5NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 360.4 ± 2.1 | kcal/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 353.4 ± 2.0 | kcal/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: C4H4N- + C2H5NO = (C4H4N- • C2H5NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 26. ± 2. | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 31. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
By formula: C2H4NO- + C2H5NO = (C2H4NO- • C2H5NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 28. ± 2. | kcal/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 31. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
By formula: Li+ + C2H5NO = (Li+ • C2H5NO)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
39.6 | 373. | CIDC | Herreros, Gal, et al., 1999 | RCD |
Mass spectrum (electron ionization)
Go To: Top, Phase change data, Reaction thermochemistry 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 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 | J.A.GILPIN DOW CHEM. CO., MIDLAND, MICHIGAN, USA |
NIST MS number | 143 |
Gas Chromatography
Go To: Top, Phase change data, Reaction thermochemistry 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | SE-30 | 180. | 793. | Krawczyk and Piotrowski, 1989 | N2, Chromosorb W AW; Column length: 1. m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 722. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1615. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
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]
Ushakov, Sedov, et al., 1996
Ushakov, V.S.; Sedov, S.M.; Knyazev, B.A.; Kuchkaev, B.I.,
Thermodynamic properties of N-methylformamide,
Zh. Fiz. Khim., 1996, 70, 9, 1573. [all data]
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
. [all data]
Varushchenko, 1986
Varushchenko, R.M.,
Zh. Fiz. Khim., 1986, 60, 291. [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]
Heinrich, Ilavsky, et al., 1961
Heinrich, J.; Ilavsky, J.; Surovy, J.,
Chem. Zvesti, 1961, 15, 414. [all data]
Dykyj, 1970
Dykyj, J.,
Petrochemica, 1970, 10, 2, 51. [all data]
Heinrich, Ilavsky, et al., 1961, 2
Heinrich, J.; Ilavsky, J.; Surovy, J.,
Dependence of the Vapor Pressure of N-Methylformamide from the Temperature Equilibrium Liquid-Vapor for the System N-Methyl-Formamide-Water,
Chem. Zvesti, 1961, 15, 6, 414-418. [all data]
Ahlers, Lohmann, et al., 1999
Ahlers, Jens; Lohmann, Jürgen; Gmehling, Jürgen,
Binary Solid-Liquid Equilibria of Organic Systems Containing Different Amides and Sulfolane,
J. Chem. Eng. Data, 1999, 44, 4, 727-730, https://doi.org/10.1021/je9802975
. [all data]
Taft, 1987
Taft, R.W.,
The Nature and Analysis of Substitutent Electronic Effects,
Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Meot-Ner (Mautner), 1988
Meot-Ner (Mautner), M.,
Models for Strong Interactions in Proteins and Enzymes. 2. Interactions of Ions with the Peptide Link and Imidazole,
J. Am. Chem. Soc., 1988, 110, 10, 3075, https://doi.org/10.1021/ja00218a014
. [all data]
Herreros, Gal, et al., 1999
Herreros, M.; Gal, J.-F.; Maria, P.-C.; Decouzon, M.,
Gas-Phase Basicity of Simple Amides Toward Proton and Lithium Cation: An Experimental and Theoretical Study,
Eur. J. Mass Spectrom., 1999, 5, 1, 259, https://doi.org/10.1255/ejms.282
. [all data]
Krawczyk and Piotrowski, 1989
Krawczyk, W.; Piotrowski, G.T.,
Relationships Between Structure and Retention Index for N-Substituted Amides of Aliphatic Acids on a Non-Polar Column,
J. Chromatogr., 1989, 463, 297-304, https://doi.org/10.1016/S0021-9673(01)84484-8
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
T Temperature Tboil Boiling point ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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