Acetamide
- Formula: C2H5NO
- Molecular weight: 59.0672
- IUPAC Standard InChIKey: DLFVBJFMPXGRIB-UHFFFAOYSA-N
- CAS Registry Number: 60-35-5
- 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: Acetic acid amide; Ethanamide; Methanecarboxamide; CH3CONH2; NCI-C02108; Amid kyseliny octove
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Gas phase ion energetics data
Go To: Top, 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
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) | 9.69 ± 0.07 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 206.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 199.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.7 | PE | Asbrink, Svensson, et al., 1981 | LLK |
10.15 ± 0.05 | EI | Baldwin, Loudon, et al., 1977 | LLK |
9.62 | PE | Meeks, Arnett, et al., 1975 | LLK |
9.62 | PE | McGlynn and Meeks, 1975 | LLK |
9.80 | PE | Sweigart and Turner, 1972 | LLK |
9.77 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.65 ± 0.03 | PI | Vilesov, 1960 | RDSH |
10.0 | PE | Asbrink, Svensson, et al., 1981 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH2NO+ | 11.60 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H3O+ | 11.70 | ? | EI | Loudon and Webb, 1977 | LLK |
De-protonation reactions
C2H4NO- + =
By formula: C2H4NO- + H+ = C2H5NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 362.0 ± 2.1 | kcal/mol | G+TS | Decouzon, Exner, et al., 1990 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 358.6 ± 1.2 | kcal/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 355.0 ± 2.0 | kcal/mol | IMRE | Decouzon, Exner, et al., 1990 | gas phase; value altered from reference due to change in acidity scale; B |
C2H4NO- + =
By formula: C2H4NO- + H+ = C2H5NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 373.0 ± 3.1 | kcal/mol | G+TS | Hare, Marimanikkuppam, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 365.0 ± 3.0 | kcal/mol | IMRB | Hare, Marimanikkuppam, et al., 2001 | gas phase; B |
References
Go To: Top, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Asbrink, Svensson, et al., 1981
Asbrink, L.; Svensson, A.; Von Niessen, W.; Bieri, G.,
30.4 nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1981, 24, 293. [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]
Meeks, Arnett, et al., 1975
Meeks, J.L.; Arnett, J.F.; Larson, D.; McGlynn, S.P.,
Photoelectron spectroscopy of carbonyls. Ionization assignments,
Chem. Phys. Lett., 1975, 30, 190. [all data]
McGlynn and Meeks, 1975
McGlynn, S.P.; Meeks, J.L.,
Photoelectron spectra of carbonyls: Acetaldehyde, acetamide, biacetyl, pyruvic acid, methyl pyruvate and vamide,
J. Electron Spectrosc. Relat. Phenom., 1975, 6, 269. [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]
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]
Vilesov, 1960
Vilesov, F.I.,
The photoionization of vapors of compounds whose molecules contain carbonyl groups,
Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [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]
Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A.,
Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry,
Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C
. [all data]
Hare, Marimanikkuppam, et al., 2001
Hare, M.C.; Marimanikkuppam, S.S.; Kass, S.R.,
Acetamide enolate: formation, reactivity, and proton affinity,
Int. J. Mass Spectrom., 2001, 210, 153-163, https://doi.org/10.1016/S1387-3806(01)00397-9
. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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