phenoxide 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

phenoxide anion + Hydrogen cation = Phenol

By formula: C6H5O- + H+ = C6H6O

Quantity Value Units Method Reference Comment
Δr349. ± 2.kcal/molAVGN/AAverage of 6 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Δr342.3 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; Shiner, Vorner, et al., 1986: tautomer acidities ΔHacid(ortho) = 343.9±3.1 kcal, para = 340.1±2 kcal. However, Capponi, Gut, et al., 1999 based on aq. soln. results, imply 18 and 14 kcal/mol difference.; value altered from reference due to change in acidity scale; B
Δr340.8 ± 1.9kcal/molCIDCAngel and Ervin, 2004gas phase; B
Δr343.4 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B
Δr>341.5 ± 1.8kcal/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

phenoxide anion + Acetic acid = (phenoxide anion • Acetic acid)

By formula: C6H5O- + C2H4O2 = (C6H5O- • C2H4O2)

Quantity Value Units Method Reference Comment
Δr27.4kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M
Quantity Value Units Method Reference Comment
Δr24.0cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M

phenoxide anion + Water = (phenoxide anion • Water)

By formula: C6H5O- + H2O = (C6H5O- • H2O)

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Δr15.4kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr23.9cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M

phenoxide anion + Water = C6H7O2-

By formula: C6H5O- + H2O = C6H7O2-

Quantity Value Units Method Reference Comment
Δr15.4 ± 1.0kcal/molN/AMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Δr8.2 ± 1.6kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B

phenoxide anion + Ethanol = C8H11O2-

By formula: C6H5O- + C2H6O = C8H11O2-

Quantity Value Units Method Reference Comment
Δr19.3 ± 1.0kcal/molN/AMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Δr11.2 ± 1.6kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B

phenoxide anion + Ethanol = (phenoxide anion • Ethanol)

By formula: C6H5O- + C2H6O = (C6H5O- • C2H6O)

Quantity Value Units Method Reference Comment
Δr19.3kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr27.0cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; 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

Protonation reactions

phenoxide anion + Hydrogen cation = Phenol

By formula: C6H5O- + H+ = C6H6O

Quantity Value Units Method Reference Comment
Δr349. ± 2.kcal/molAVGN/AAverage of 6 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Δr342.3 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; Shiner, Vorner, et al., 1986: tautomer acidities ΔHacid(ortho) = 343.9±3.1 kcal, para = 340.1±2 kcal. However, Capponi, Gut, et al., 1999 based on aq. soln. results, imply 18 and 14 kcal/mol difference.; value altered from reference due to change in acidity scale
Δr340.8 ± 1.9kcal/molCIDCAngel and Ervin, 2004gas phase
Δr343.4 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase
Δr>341.5 ± 1.8kcal/molH-TSRichardson, Stephenson, et al., 1975gas 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.

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Shiner, Vorner, et al., 1986
Shiner, C.S.; Vorner, P.E.; Kass, S.R., Gas phase acidities and heats of formation of 2,4- and 2,5- cyclohexadien-1-one, the keto tautomers of phenol, J. Am. Chem. Soc., 1986, 108, 5699. [all data]

Capponi, Gut, et al., 1999
Capponi, M.; Gut, I.G.; Hellrung, B.; Persy, G.; Wirz, J., Ketonization equilibria of phenol in aqueous solution, Can. J. Chem., 1999, 77, 5-6, 605-613, https://doi.org/10.1139/v99-048 . [all data]

Angel and Ervin, 2004
Angel, L.A.; Ervin, K.M., Competitive threshold collision-induced dissociation: Gas-phase acidity and O-H bond dissociation enthalpy of phenol, J. Phys. Chem. A, 2004, 108, 40, 8346-8352, https://doi.org/10.1021/jp0474529 . [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]

Richardson, Stephenson, et al., 1975
Richardson, J.H.; Stephenson, L.M.; Brauman, J.I., Photodetachment of electrons from phenoxides and thiophenoxide, J. Am. Chem. Soc., 1975, 97, 2967. [all data]

Meot-Ner and Sieck, 1986
Meot-Ner, M.; Sieck, L.W., The ionic hydrogen bond and ion solvation. 5. OH...O- bonds. Gas phase solvation and clustering of alkoxide and carboxylate anions, J. Am. Chem. Soc., 1986, 108, 7525. [all data]


Notes

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