benzoate anion
- Formula: C7H5O2-
- Molecular weight: 121.1139
- IUPAC Standard InChI: InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)/p-1
- IUPAC Standard InChIKey: WPYMKLBDIGXBTP-UHFFFAOYSA-M
- CAS Registry Number: 766-76-7
- Chemical structure:
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
+
=
By formula: C7H5O2- + H+ = C7H6O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 340.1 ± 2.2 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 340.0 ± 2.9 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; Recalculated from data in paper; error in Table vs. ladder; B |
| ΔrH° | 340.2 ± 2.2 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 333.0 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 332.9 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; Recalculated from data in paper; error in Table vs. ladder; B |
| ΔrG° | 333.1 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
( • 2
) +
= (
• 3
)
By formula: (C7H5O2- • 2H2O) + H2O = (C7H5O2- • 3H2O)
Bond type: Hydrogen bond (negative ion to hydride)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 11.5 ± 1.5 | kcal/mol | TDAs | Blades, Klassen, et al., 1995 | gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 4.50 ± 0.30 | kcal/mol | TDAs | Blades, Klassen, et al., 1995 | gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B,M |
( •
) +
= (
• 2
)
By formula: (C7H5O2- • H2O) + H2O = (C7H5O2- • 2H2O)
Bond type: Hydrogen bond (negative ion to hydride)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 12.7 ± 1.5 | kcal/mol | TDAs | Blades, Klassen, et al., 1995 | gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 5.70 ± 0.30 | kcal/mol | TDAs | Blades, Klassen, et al., 1995 | gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B,M |
+
= (
•
)
By formula: C7H5O2- + H2O = (C7H5O2- • H2O)
Bond type: Hydrogen bond (negative ion to hydride)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.1 ± 1.5 | kcal/mol | TDAs | Blades, Klassen, et al., 1995 | gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 8.10 ± 0.30 | kcal/mol | TDAs | Blades, Klassen, et al., 1995 | gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B,M |
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 |
|---|---|---|---|
| <3.590 ± 0.050 | LPES | Woo, Wang, et al., 2005 | Implies BDE <109.3±3.3 |
| 3.60 ± 0.10 | LPES | Wang, Nicholas, et al., 2000 | |
| 3.75 ± 0.16 | D-EA | Fujio, McIver, et al., 1981 | value altered from reference due to change in acidity scale |
Protonation reactions
+
=
By formula: C7H5O2- + H+ = C7H6O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 340.1 ± 2.2 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale |
| ΔrH° | 340.0 ± 2.9 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; Recalculated from data in paper; error in Table vs. ladder |
| ΔrH° | 340.2 ± 2.2 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 333.0 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale |
| ΔrG° | 332.9 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; Recalculated from data in paper; error in Table vs. ladder |
| ΔrG° | 333.1 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase |
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.
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [all data]
Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P.,
Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria,
Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092
. [all data]
Blades, Klassen, et al., 1995
Blades, A.T.; Klassen, J.S.; Kebarle, P.,
Free Energies of Hydration in the Gas Phase on the Anions of Some Oxo Acids of C, N, S, P, Cl and I,
J. Am. Chem. Soc., 1995, 117, 42, 10563, https://doi.org/10.1021/ja00147a019
. [all data]
Woo, Wang, et al., 2005
Woo, H.K.; Wang, X.B.; Kiran, B.; Wang, L.S.,
Temperature-dependent photoelectron spectroscopy of methyl benzoate anions: Observation of steric effect in o-methyl benzoate,
J. Phys. Chem. A, 2005, 109, 50, 11395-11400, https://doi.org/10.1021/jp0529467
. [all data]
Wang, Nicholas, et al., 2000
Wang, X.B.; Nicholas, J.B.; Wang, L.S.,
Intramolecular Coulomb repulsion and anisotropies of the repulsive Coulomb barrier in multiply charged anions,
J. Chem. Phys., 2000, 113, 2, 653-661, https://doi.org/10.1063/1.481842
. [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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