NCCH=C(OMe)O anion


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 by: John E. Bartmess

Protonation reactions

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

By formula: C4H4NO2- + H+ = C4H5NO2

Quantity Value Units Method Reference Comment
Δr1426. ± 8.8kJ/molG+TSMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.
Δr1425. ± 8.8kJ/molG+TSTaft, Abboud, et al., 1988gas phase
Quantity Value Units Method Reference Comment
Δr1400. ± 8.4kJ/molIMREMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.
Δr1399. ± 8.4kJ/molIMRETaft, Abboud, et al., 1988gas phase

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.

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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