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benzoate anion


Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, Ion clustering 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

benzoate anion + Hydrogen cation = Benzoic acid

By formula: C7H5O2- + H+ = C7H6O2

Quantity Value Units Method Reference Comment
Deltar1423. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1423. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder; B
Deltar1423. ± 9.2kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar1393. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1393. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder; B
Deltar1394. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; B

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

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

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Deltar48.1 ± 6.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B
Quantity Value Units Method Reference Comment
Deltar18.8 ± 1.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B,M

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

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

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Deltar53.1 ± 6.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B
Quantity Value Units Method Reference Comment
Deltar23.8 ± 1.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B,M

benzoate anion + Water = (benzoate anion bullet Water)

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

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Deltar63.2 ± 6.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B
Quantity Value Units Method Reference Comment
Deltar33.9 ± 1.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B,M

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Ion clustering 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 ± 0.050LPESWoo, 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
Deltar1423. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1423. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder
Deltar1423. ± 9.2kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Quantity Value Units Method Reference Comment
Deltar1393. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1393. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder
Deltar1394. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase

Ion clustering data

Go To: Top, Reaction thermochemistry data, 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

benzoate anion + Water = (benzoate anion bullet Water)

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

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Deltar63.2 ± 6.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B
Quantity Value Units Method Reference Comment
Deltar33.9 ± 1.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B,M

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

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

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Deltar53.1 ± 6.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B
Quantity Value Units Method Reference Comment
Deltar23.8 ± 1.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B,M

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

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

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Deltar48.1 ± 6.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B
Quantity Value Units Method Reference Comment
Deltar18.8 ± 1.3kJ/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B,M

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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, Ion clustering data, References