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 Copy

  
• IUPAC Standard InChIKey: WPYMKLBDIGXBTP-UHFFFAOYSA-M Copy
• CAS Registry Number: 766-76-7
• Chemical structure:
  This structure is also available as a 2d Mol file
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
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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 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

( • 2) +  = ( • 3)

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

Bond type: Hydrogen bond (negative ion to hydride)

( • ) +  = ( • 2)

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

Bond type: Hydrogen bond (negative ion to hydride)

 +  = ( • )

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

Bond type: Hydrogen bond (negative ion to hydride)

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

Protonation reactions

 +  =

By formula: C₇H₅O₂^- + H⁺ = C₇H₆O₂

Ion clustering 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

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

 +  = ( • )

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

Bond type: Hydrogen bond (negative ion to hydride)

( • ) +  = ( • 2)

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

Bond type: Hydrogen bond (negative ion to hydride)

( • 2) +  = ( • 3)

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

Bond type: Hydrogen bond (negative ion to hydride)

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

• 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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