Acetamide

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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)9.69 ± 0.07eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)206.4kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity199.0kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.7PEAsbrink, Svensson, et al., 1981LLK
10.15 ± 0.05EIBaldwin, Loudon, et al., 1977LLK
9.62PEMeeks, Arnett, et al., 1975LLK
9.62PEMcGlynn and Meeks, 1975LLK
9.80PESweigart and Turner, 1972LLK
9.77 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
9.65 ± 0.03PIVilesov, 1960RDSH
10.0PEAsbrink, Svensson, et al., 1981Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH2NO+11.60?EILoudon and Webb, 1977LLK
C2H3O+11.70?EILoudon and Webb, 1977LLK

De-protonation reactions

C2H4NO- + Hydrogen cation = Acetamide

By formula: C2H4NO- + H+ = C2H5NO

Quantity Value Units Method Reference Comment
Δr362.0 ± 2.1kcal/molG+TSDecouzon, Exner, et al., 1990gas phase; value altered from reference due to change in acidity scale; B
Δr358.6 ± 1.2kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Δr355.0 ± 2.0kcal/molIMREDecouzon, Exner, et al., 1990gas phase; value altered from reference due to change in acidity scale; B

C2H4NO- + Hydrogen cation = Acetamide

By formula: C2H4NO- + H+ = C2H5NO

Quantity Value Units Method Reference Comment
Δr373.0 ± 3.1kcal/molG+TSHare, Marimanikkuppam, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Δr365.0 ± 3.0kcal/molIMRBHare, Marimanikkuppam, et al., 2001gas 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

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