pCO2H-phenoxide anion
- Formula: C7H5O3-
- Molecular weight: 137.1133
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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 by: John E. Bartmess
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Individual Reactions
C7H5O3- + =
By formula: C7H5O3- + H+ = C7H6O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 335.9 ± 2.1 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; This is probably the phenolic site acidity, not the carboxylic. |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 328.9 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; This is probably the phenolic site acidity, not the carboxylic. |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, References, Notes
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 ± 0.10 | LPES | Tian, Wang, et al., 2009 | Vertical Detachment Energy: 3.0±0.1 eV. |
Protonation reactions
C7H5O3- + =
By formula: C7H5O3- + H+ = C7H6O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 335.9 ± 2.1 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; This is probably the phenolic site acidity, not the carboxylic. |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 328.9 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas 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
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
EAneutral Electron affinity of neutral species ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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