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Acetamide, N-phenyl-

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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

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

By formula: C8H8NO- + H+ = C8H9NO

Quantity Value Units Method Reference Comment
Deltar1454. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Deltar1476. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar1425. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; B
Deltar1447. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

Acetamide, N-phenyl- + Acetic acid = C10H11NO2 + Water

By formula: C8H9NO + C2H4O2 = C10H11NO2 + H2O

Quantity Value Units Method Reference Comment
Deltar45.5 ± 0.3kJ/molCmWadso, 1965solid phase; Heat of hydrolysis; ALS

Acetamide, N-phenyl- + Water = Aniline + Acetic acid

By formula: C8H9NO + H2O = C6H7N + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-42.0 ± 0.3kJ/molCmWadso, 1965solid phase; Heat of hydrolysis; ALS

1-[1,2,4]Triazol-1-ylethanone + Aniline = Acetamide, N-phenyl- + 1H-1,2,4-Triazole

By formula: C4H5N3O + C6H7N = C8H9NO + C2H3N3

Quantity Value Units Method Reference Comment
Deltar-72.3 ± 0.3kJ/molCmWadso, 1962solid phase; ALS

1-Acetyl-1H-tetrazole + Aniline = Acetamide, N-phenyl- + 1H-Tetrazole

By formula: C3H4N4O + C6H7N = C8H9NO + CH2N4

Quantity Value Units Method Reference Comment
Deltar-84.6 ± 0.3kJ/molCmWadso, 1962solid phase; ALS

Acetic anhydride + Aniline = Acetamide, N-phenyl- + Acetic acid

By formula: C4H6O3 + C6H7N = C8H9NO + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-100.9 ± 0.3kJ/molCmWadso, 1962liquid phase; ALS

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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, https://doi.org/10.1021/ar00156a005 . [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]

Wadso, 1965
Wadso, I., Thermochemical properties of diacetimide, N-butyldiacetimide and N-phenyldiacetimide, Acta Chem. Scand., 1965, 19, 1079-1087. [all data]

Wadso, 1962
Wadso, I., Heats of aminolysis and hydrolysis of some N-acetyl compounds and of acetic anhydride, Acta Chem. Scand., 1962, 16, 471-478. [all data]


Notes

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