Acetamide, N-methyl-
- Formula: C3H7NO
- Molecular weight: 73.0938
- IUPAC Standard InChIKey: OHLUUHNLEMFGTQ-UHFFFAOYSA-N
- CAS Registry Number: 79-16-3
- 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: Methylacetamide; Monomethylacetamide; N-Methylacetamide; CH3CONHCH3; Acetylmethylamine; N-Acetyl-N-methylamine; X 44
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Gas phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -248.0 ± 5.5 | kJ/mol | Ccb | Roux, Jimenez, et al., 1996 |
Condensed phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -313.2 ± 1.3 | kJ/mol | Ccb | Vasil'eva and Zhil'tsova, 1982 | hf298 calculated possible error by authors |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1867.7 ± 1.3 | kJ/mol | Ccb | Vasil'eva and Zhil'tsova, 1982 | hf298 calculated possible error by authors |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | -318.8 ± 5.1 | kJ/mol | Ccb | Roux, Jimenez, et al., 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1862.1 ± 5.1 | kJ/mol | Ccb | Roux, Jimenez, et al., 1996 |
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
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 478.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 303.43 | K | N/A | Casteel and Amis, 1974 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 302.90 | K | N/A | Boje and Hvidt, 1971 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 303.67 | K | N/A | Bonner and Kim, 1970 | Uncertainty assigned by TRC = 0.15 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 70.8 ± 2.0 | kJ/mol | V | Roux, Jimenez, et al., 1996 | ALS |
ΔsubH° | 70.8 ± 2.0 | kJ/mol | N/A | Roux, Jimenez, et al., 1996 | AC |
ΔsubH° | 69.87 ± 0.31 | kJ/mol | N/A | Starzewski, Wadso, et al., 1984 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
55.5 | 378. | N/A | Schmelzer and Pusch, 1995 | Based on data from 363. to 414. K.; AC |
62. | 368. | N/A | Aucejo, Monton, et al., 1993 | Based on data from 353. to 428. K.; AC |
59.6 | 348. | A | Stephenson and Malanowski, 1987 | Based on data from 333. to 443. K.; AC |
53.5 | 368. | A | Stephenson and Malanowski, 1987 | Based on data from 353. to 479. K.; 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 |
---|---|---|---|---|---|
313. to 363. | -0.06922 | 144.114 | -277.873 | Gopal and Rizvi, 1968 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
54.0 | 288. to 303. | Aihara, 1952 | See also Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.11 | 303.7 | Ahlers, Lohmann, et al., 1999 | AC |
9.73 | 303.8 | Kreis and Wood, 1969 | AC |
Reaction thermochemistry 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:
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
By formula: C2H3O2- + C3H7NO = (C2H3O2- • C3H7NO)
Bond type: Hydrogen bonds of deprotonated acids to amides
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 106. ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 115. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 72.0 ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B |
By formula: C4H4N- + C3H7NO = (C4H4N- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 110. | 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 |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
49.8 | 497. | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
By formula: C3H6NO- + C3H7NO = (C3H6NO- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 110. | 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 |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
52.3 | 497. | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
By formula: (C2H3O2- • C3H7NO) + C3H7NO = (C2H3O2- • 2C3H7NO)
Bond type: Hydrogen bonds of deprotonated acids to amides
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 73.6 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 91.2 | J/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
By formula: C3H8NO+ + C3H7NO = (C3H8NO+ • C3H7NO)
Bond type: Hydrogen bonds of the type OH-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 125. | kJ/mol | PHPMS | Meot-Ner, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 98.7 | J/mol*K | PHPMS | Meot-Ner, 1984 | gas phase; M |
C3H6NO- + =
By formula: C3H6NO- + H+ = C3H7NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1514. ± 9.2 | kJ/mol | G+TS | Decouzon, Exner, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1483. ± 8.4 | kJ/mol | IMRE | Decouzon, Exner, et al., 1990 | gas phase; B |
By formula: Li+ + C3H7NO = (Li+ • C3H7NO)
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
173. | 373. | CIDT,ICR | Herreros, Gal, et al., 1999 | RCD |
By formula: Na+ + C3H7NO = (Na+ • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 149. | kJ/mol | CIDT | Klassen, Anderson, et al., 1996 | RCD |
By formula: K+ + C3H7NO = (K+ • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 127. | kJ/mol | CIDT | Klassen, Anderson, et al., 1996 | RCD |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Roux, Jimenez, et al., 1996
Roux, M.V.; Jimenez, P.; Davalos, J.Z.; Castano, O.; Molina, M.T.; Notario, R.; Herreros, M.; Abboud, J.-L.M.,
The first direct experimental determination of strain in neutral and protonated 2-azetidinone,
J. Am. Chem. Soc., 1996, 118, 12735-12737. [all data]
Vasil'eva and Zhil'tsova, 1982
Vasil'eva, T.F.; Zhil'tsova, E.N.,
Heat of combustion of two monomethylamides,
Termodin. Organ. Soedin., 1982, 108-110. [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]
Casteel and Amis, 1974
Casteel, J.F.; Amis, E.S.,
Conductance of Sodium Perchlorate in Water-N-Methylacetamide (NMA) Solvent System,
J. Chem. Eng. Data, 1974, 19, 121. [all data]
Boje and Hvidt, 1971
Boje, L.; Hvidt, A.,
Densities of aqueous mixtures of non-electrolytes,
J. Chem. Thermodyn., 1971, 3, 663. [all data]
Bonner and Kim, 1970
Bonner, O.D.; Kim, S.J.,
Intermolecular Association in Structured Liquids 1. Ethylene Carbonate and N-Methylacetamide,
J. Chem. Thermodyn., 1970, 2, 63. [all data]
Starzewski, Wadso, et al., 1984
Starzewski, P.; Wadso, I.; Zielenkiewicz, W.,
Enthalpies of vaporization of some N-alkylamides at 298.15 K,
J. Chem. Thermodyn., 1984, 16, 331-334. [all data]
Schmelzer and Pusch, 1995
Schmelzer, Jürgen; Pusch, Jens,
Phase equilibria in binary systems containing N-monosubstituted amides and hydrocarbons,
Fluid Phase Equilibria, 1995, 110, 1-2, 183-196, https://doi.org/10.1016/0378-3812(95)02753-2
. [all data]
Aucejo, Monton, et al., 1993
Aucejo, Antonio; Monton, Juan B.; Munoz, Rosa; Sanchotello, Margarita,
Isobaric vapor-liquid equilibrium data for the cyclohexanone + N-methylacetamide system,
J. Chem. Eng. Data, 1993, 38, 1, 160-162, https://doi.org/10.1021/je00009a039
. [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]
Gopal and Rizvi, 1968
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]
Aihara, 1952
Aihara, A.,
J. Chem. Soc. Jpn. Pure Chem. Sect., 1952, 73, 855. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [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]
Kreis and Wood, 1969
Kreis, R.W.; Wood, R.H.,
Enthalpy of fusion and cryoscopic constant of N-methylacetamide,
The Journal of Chemical Thermodynamics, 1969, 1, 6, 523-526, https://doi.org/10.1016/0021-9614(69)90012-3
. [all data]
Meot-ner, 1988
Meot-ner, M.,
Ionic Hydrogen Bond and Ion Solvation. 6. Interaction Energies of the Acetate Ion with Organic Molecules. Comparison of CH3COO- with Cl-, CN-, and SH-,
J. Am. Chem. Soc., 1988, 110, 12, 3854, https://doi.org/10.1021/ja00220a022
. [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]
Meot-Ner, 1984
Meot-Ner, (Mautner),
The Ionic Hydrogen Bond. 4. Intramolecular and Multiple Bonds. Proton Affinities, Hydration and Complexes of Amides and Amino Acid Derivatives,
J. Am. Chem. Soc., 1984, 106, 2, 278, https://doi.org/10.1021/ja00314a003
. [all data]
Decouzon, Exner, et al., 1990
Decouzon, M.; Exner, O.; Gal, J.-F.; Maria, P.-C.,
The Gas-Phase Acidity and the Acidic Site of Acetohydroxamic Acid: an FT-ICR Study,
J. Org. Chem., 1990, 55, 13, 3980, https://doi.org/10.1021/jo00300a007
. [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]
Klassen, Anderson, et al., 1996
Klassen, J.S.; Anderson, S.G.; Blades, A.T.; Kebarle, P.,
Reaction Enthalpies for M+L = M+ + L, Where M+ = Na+ and K+ and L = Acetamide, N-Methylacetamide, N,N-Dimethylacetamide, Glycine, and Glycylglycine, from Determinations of the Collision-Induced Dissociation Thresholds,
J. Phys. Chem., 1996, 100, 33, 14218, https://doi.org/10.1021/jp9608382
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions 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 ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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