Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

benzoate anion


Gas phase ion energetics data

Go To: Top, 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
Deltar340.1 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar340.0 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder
Deltar340.2 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Quantity Value Units Method Reference Comment
Deltar333.0 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar332.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder
Deltar333.1 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase

References

Go To: Top, 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.

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]

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]


Notes

Go To: Top, Gas phase ion energetics data, References