benzoate 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Individual Reactions

benzoate anion + Hydrogen cation = Benzoic acid

By formula: C7H5O2- + H+ = C7H6O2

Quantity Value Units Method Reference Comment
Δr340.1 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr340.0 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder; B
Δr340.2 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr333.0 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr332.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder; B
Δr333.1 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B

(benzoate anion • 2Water) + Water = (benzoate anion • 3Water)

By formula: (C7H5O2- • 2H2O) + H2O = (C7H5O2- • 3H2O)

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Δr11.5 ± 1.5kcal/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B
Quantity Value Units Method Reference Comment
Δr4.50 ± 0.30kcal/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B,M

(benzoate anion • Water) + Water = (benzoate anion • 2Water)

By formula: (C7H5O2- • H2O) + H2O = (C7H5O2- • 2H2O)

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Δr12.7 ± 1.5kcal/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B
Quantity Value Units Method Reference Comment
Δr5.70 ± 0.30kcal/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B,M

benzoate anion + Water = (benzoate anion • Water)

By formula: C7H5O2- + H2O = (C7H5O2- • H2O)

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Δr15.1 ± 1.5kcal/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B
Quantity Value Units Method Reference Comment
Δr8.10 ± 0.30kcal/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. ΔSaff approx. 24 cal/mol-K; B,M

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
<3.590 ± 0.050LPESWoo, Wang, et al., 2005Implies BDE <109.3±3.3
3.60 ± 0.10LPESWang, Nicholas, et al., 2000 
3.75 ± 0.16D-EAFujio, McIver, et al., 1981value altered from reference due to change in acidity scale

Protonation reactions

benzoate anion + Hydrogen cation = Benzoic acid

By formula: C7H5O2- + H+ = C7H6O2

Quantity Value Units Method Reference Comment
Δr340.1 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr340.0 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder
Δr340.2 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Quantity Value Units Method Reference Comment
Δr333.0 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr332.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder
Δr333.1 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas 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.

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

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