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Acetic acid, cyano-, methyl ester

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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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

Ionization energy determinations

IE (eV) Method Reference Comment
10.87 ± 0.05EIPignataro, Foffani, et al., 1966RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O2+10.40 ± 0.02C2H2NEIHolmes, Lossing, et al., 1993LL
C2H3O2+11.72 ± 0.03?EIBriggs and Shannon, 1969RDSH

De-protonation reactions

C4H4NO2- + Hydrogen cation = Acetic acid, cyano-, methyl ester

By formula: C4H4NO2- + H+ = C4H5NO2

Quantity Value Units Method Reference Comment
Deltar1426. ± 8.8kJ/molG+TSMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.; B
Deltar1425. ± 8.8kJ/molG+TSTaft, Abboud, et al., 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar1400. ± 8.4kJ/molIMREMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.; B
Deltar1399. ± 8.4kJ/molIMRETaft, Abboud, et al., 1988gas 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.

Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G., Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH2-R, Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [all data]

Holmes, Lossing, et al., 1993
Holmes, J.L.; Lossing, F.P.; Mayer, P.M., The effects of methyl substitution on the structure and thermochemistry of the cyanomethyl radical and cation, Chem. Phys. Lett., 1993, 212, 134. [all data]

Briggs and Shannon, 1969
Briggs, P.R.; Shannon, T.W., The heat of formation of the methoxycarbonyl ion, J. Am. Chem. Soc., 1969, 91, 4307. [all data]

Mishima, Matsuoka, et al., 2004
Mishima, M.; Matsuoka, M.; Lei, Y.X.; Rappoport, Z., Gas-phase acidities of disubstituted methanes and of enols of carboxamides substituted by electron-withdrawing groups, J. Org. Chem., 2004, 69, 18, 5947-5965, https://doi.org/10.1021/jo040196b . [all data]

Taft, Abboud, et al., 1988
Taft, R.W.; Abboud, J.L.M.; Anvia, F.; Berthelot, M.; Fujio, M.; Gal, J.-F.; Headley, A.D.; Henderson, W.G., Regarding the Inherent Dependence of Resonance Effects of Strongly Conjugated Substituents on Electron Demand, J. Am. Chem. Soc., 1988, 110, 6, 1797, https://doi.org/10.1021/ja00214a023 . [all data]


Notes

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