pCO2H-phenoxide anion


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 by: John E. Bartmess

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Individual Reactions

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

By formula: C7H5O3- + H+ = C7H6O3

Quantity Value Units Method Reference Comment
Δr335.9 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.
Quantity Value Units Method Reference Comment
Δr328.9 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.

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
Δr335.9 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.
Quantity Value Units Method Reference Comment
Δr328.9 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.

References

Go To: Top, Reaction thermochemistry data, 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.

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]

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]


Notes

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