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pCO2H-phenoxide 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

Electron affinity of neutral species

EAneutral (eV) Method Reference Comment
2.85 ± 0.10LPESTian, Wang, et al., 2009Vertical Detachment Energy: 3.0±0.1 eV.

Protonation reactions

C7H5O3- + Hydrogen cation = Benzoic acid, 4-hydroxy-

By formula: C7H5O3- + H+ = C7H6O3

Quantity Value Units Method Reference Comment
Deltar335.9 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.
Quantity Value Units Method Reference Comment
Deltar328.9 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.

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.

Tian, Wang, et al., 2009
Tian, Z.X.; Wang, X.B.; Wang, L.S.; Kass, S.R., Are Carboxyl Groups the Most Acidic Sites in Amino Acids? Gas-Phase Acidities, Photoelectron Spectra, and Computations on Tyrosine, p-Hydroxybenzoic Acid, and Their Conjugate Bases, J. Am. Chem. Soc., 2009, 131, 3, 1174-1181, https://doi.org/10.1021/ja807982k . [all data]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]


Notes

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