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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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering 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: Eugene S. Domalski and Elizabeth D. Hearing
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference |
---|---|---|
126.63 | 308. | Kulikov, Krestov, et al., 1989 |
125.2 | 298.15 | de Visser and Somsen, 1979 |
122. | 298.15 | Bonner and Cerutti, 1976 |
123.8 | 298.15 | Skold, Suurkuusk, et al., 1976 |
126.1 | 298.15 | de Visser and Somsen, 1974 |
Phase change data
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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° | 56.19 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 54.4 ± 1.3 | kJ/mol | N/A | Ushakov, Sedov, et al., 1996 | Based on data from 340. to 440. K.; AC |
ΔvapH° | 56.2 | kJ/mol | A | Barone, Castronuovo, et al., 1985 | See also Varushchenko, 1986.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
53.8 | 355. | N/A | Ushakov, Sedov, et al., 1996 | Based on data from 340. to 440. K.; AC |
54.5 | 325. | A | Stephenson and Malanowski, 1987 | Based on data from 310. to 391. K.; AC |
53.4 | 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 (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
369.6 to 472.4 | 4.99796 | 2134.031 | -45.071 | Heinrich, Ilavsky, et al., 1961, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.44 | 270.6 | Ahlers, Lohmann, et al., 1999 | AC |
Gas phase ion energetics data
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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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.83 ± 0.04 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 851.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 820.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Reference | Comment |
---|---|---|
0.0157 | Desfrancois, Periquet, et al., 1999 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.86 | PE | Kimura, Katsumata, et al., 1981 | LLK |
10.00 ± 0.05 | EI | Baldwin, Loudon, et al., 1977 | LLK |
9.79 | PE | Brundle, Turner, et al., 1969 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 12.40 | ? | EI | Loudon and Webb, 1977 | LLK |
CH4N+ | 11.65 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H4NO+ | 11.20 | ? | EI | Loudon and Webb, 1977 | LLK |
De-protonation reactions
C2H4NO- + =
By formula: C2H4NO- + H+ = C2H5NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1508. ± 8.8 | kJ/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° | 1479. ± 8.4 | kJ/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Ion clustering data
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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:
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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C2H4NO- + C2H5NO = (C2H4NO- • C2H5NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 120. ± 8. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 130. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
By formula: C4H4N- + C2H5NO = (C4H4N- • C2H5NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 110. ± 8. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 130. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
By formula: Li+ + C2H5NO = (Li+ • C2H5NO)
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
166. | 373. | CIDC | Herreros, Gal, et al., 1999 | RCD |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering 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 | J.A.GILPIN DOW CHEM. CO., MIDLAND, MICHIGAN, USA |
NIST MS number | 143 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering 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.
Kulikov, Krestov, et al., 1989
Kulikov, M.V.; Krestov, A.G.; Safonova, L.P.; Kolker, A.M.,
Excess thermodynamic functions in the systems water + N-methylformamide, and water + N,N-dimethylformamide, Sbornik Nauch Trud., Termodin. rast. neelect., Ivanovo,
Inst. nevod. rast., 1989, Akad. [all data]
de Visser and Somsen, 1979
de Visser, C.; Somsen, G.,
Thermochemical behavior of mixtures of N,N-dimethylformamide with dimethylsulfoxide, acetonitrile, and N-methylformamide: volumes and heat capacities,
J. Solution Chem., 1979, 8, 593-600. [all data]
Bonner and Cerutti, 1976
Bonner, O.D.; Cerutti, P.J.,
The partial molar heat capacities of some solutes in water and deuterium oxide,
J. Chem. Thermodynam., 1976, 8, 105-111. [all data]
Skold, Suurkuusk, et al., 1976
Skold, R.; Suurkuusk, J.; Wadso, I.,
Thermochemistry of solutions of biochemical model compounds. 7. Aqueous solutions of some amides, t-butanol, and pentanol,
J. Chem. Thermodynam., 1976, 8, 1075-1080. [all data]
de Visser and Somsen, 1974
de Visser, C.; Somsen, G.,
Molar heat capacities of binary mixtures of water and some amides at 298.15 K,
Z. Physik. Chem. [N.F.], 1974, 92, 159-162. [all data]
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]
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]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [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]
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,
Org. Mass Spectrom., 1977, 12, 283. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering 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 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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