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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Condensed phase thermochemistry data
Go To: Top, Phase change data, 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 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
Go To: Top, Condensed phase thermochemistry data, 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:
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)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
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 |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, 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
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
View reactions leading to C3H7NO+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 888.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 857.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.70 ± 0.05 | EI | Baldwin, Loudon, et al., 1977 | LLK |
8.90 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
~9.85 | PE | Sweigart and Turner, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH4N+ | 11.50 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H3O+ | 12.40 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H4NO+ | 11.80 | ? | EI | Loudon and Webb, 1977 | LLK |
De-protonation reactions
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 |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, 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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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 | Japan AIST/NIMC Database- Spectrum MS-NW-4322 |
NIST MS number | 230310 |
References
Go To: Top, Condensed phase thermochemistry data, 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.
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]
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]
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]
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]
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]
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]
Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W.,
Lone pair orbitals and their interactions studied by photoelectron spectroscopy. I. Carboxylic acids and their derivatives,
J. Am. Chem. Soc., 1972, 94, 5592. [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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy 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°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 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.