Acetamide, N-phenyl-

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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 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

Ionization energy determinations

IE (eV) Method Reference Comment
8.30 ± 0.10PEBouchoux, 1978LLK
8.60EIBaldwin, Loudon, et al., 1976LLK
8.18 ± 0.03EIBenezra and Bursey, 1971LLK
8.39 ± 0.10EICotter, 1964RDSH
8.46PENakagaki, Kobayashi, et al., 1980Vertical value; LLK
8.46 ± 0.05PESzepes, Distefano, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+13.22 ± 0.03?EIBenezra and Bursey, 1971LLK
C6H7N+10.60?EIBaldwin, Loudon, et al., 1976LLK
C6H7N+10.45 ± 0.03CH2=C=OEIBenezra and Bursey, 1971LLK
C6H7N+8.88 ± 0.15?EICotter, 1964RDSH
C8H8NO+11.00HEIBaldwin, Loudon, et al., 1976LLK

De-protonation reactions

C8H8NO- + Hydrogen cation = Acetamide, N-phenyl-

By formula: C8H8NO- + H+ = C8H9NO

Quantity Value Units Method Reference Comment
Δr347.5 ± 2.1kcal/molG+TSTaft and Bordwell, 1988gas phase; B
Δr352.8 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr340.6 ± 2.0kcal/molIMRETaft and Bordwell, 1988gas phase; B
Δr345.8 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B


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.

Bouchoux, 1978
Bouchoux, G., Ionisation et fragmentation en spectrometrie de masse VIII. Energies d'activation de deux fragmentations competitives, dissociation de l'acetate de phenyle et de l'acetanilide sous impact electronique, Int. J. Mass Spectrom. Ion Phys., 1978, 26, 379. [all data]

Baldwin, Loudon, et al., 1976
Baldwin, M.A.; Loudon, A.G.; Maccoll, A.; Webb, K.S., The nature and fragmentation pathways of the molecular ions of some arylureas, arylthioureas, acetanilides, thioacetanilides and related compounds, Org. Mass Spectrom., 1976, 11, 1181. [all data]

Benezra and Bursey, 1971
Benezra, S.A.; Bursey, M.M., ortho-Effects on ordering factors in mass spectral rearrangements. Loss of keten from halogenated phenyl acetates and acetanilides, J. Chem. Soc. B, 1971, 1515. [all data]

Cotter, 1964
Cotter, J.L., Electron impact fragmentation patterns of acetanilide and benzamide, J. Chem. Soc., 1964, 5477. [all data]

Nakagaki, Kobayashi, et al., 1980
Nakagaki, R.; Kobayashi, T.; Nagakura, S., Conformations of acetanilide and related compounds studied by ultraviolet photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1980, 53, 901. [all data]

Szepes, Distefano, et al., 1974
Szepes, L.; Distefano, G.; Pignataro, S., Steric inhibition of resonance in acetanilides by UV photoelectron spectroscopy, Ann. Chim., 1974, 64, 159. [all data]

Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G., Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase, Acc. Chem. Res., 1988, 21, 12, 463, . [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]


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