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phenoxide anion


Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, Ion clustering data, Vibrational and/or electronic energy levels, 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

phenoxide anion + Hydrogen cation = Phenol

By formula: C6H5O- + H+ = C6H6O

Quantity Value Units Method Reference Comment
Deltar349. ± 2.kcal/molAVGN/AAverage of 6 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Deltar342.3 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; Shiner, Vorner, et al., 1986: tautomer acidities «DELTA»Hacid(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
Deltar340.8 ± 1.9kcal/molCIDCAngel and Ervin, 2004gas phase; B
Deltar343.4 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B
Deltar>341.5 ± 1.8kcal/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar27.4kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M
Quantity Value Units Method Reference Comment
Deltar24.0cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M

phenoxide anion + Water = (phenoxide anion bullet Water)

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

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Deltar15.4kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar23.9cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M

phenoxide anion + Water = C6H7O2-

By formula: C6H5O- + H2O = C6H7O2-

Quantity Value Units Method Reference Comment
Deltar15.4 ± 1.0kcal/molN/AMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar8.2 ± 1.6kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B

phenoxide anion + Ethanol = C8H11O2-

By formula: C6H5O- + C2H6O = C8H11O2-

Quantity Value Units Method Reference Comment
Deltar19.3 ± 1.0kcal/molN/AMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar11.2 ± 1.6kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B

phenoxide anion + Ethanol = (phenoxide anion bullet Ethanol)

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

Quantity Value Units Method Reference Comment
Deltar19.3kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar27.0cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Ion clustering data, Vibrational and/or electronic energy levels, 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

Protonation reactions

phenoxide anion + Hydrogen cation = Phenol

By formula: C6H5O- + H+ = C6H6O

Quantity Value Units Method Reference Comment
Deltar349. ± 2.kcal/molAVGN/AAverage of 6 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Deltar342.3 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; Shiner, Vorner, et al., 1986: tautomer acidities «DELTA»Hacid(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
Deltar340.8 ± 1.9kcal/molCIDCAngel and Ervin, 2004gas phase
Deltar343.4 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase
Deltar>341.5 ± 1.8kcal/molH-TSRichardson, Stephenson, et al., 1975gas phase

Ion clustering data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess

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

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

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

Quantity Value Units Method Reference Comment
Deltar27.4kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M
Quantity Value Units Method Reference Comment
Deltar24.0cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; calculated from CH3COO-.C6H5OH; M

phenoxide anion + Ethanol = (phenoxide anion bullet Ethanol)

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

Quantity Value Units Method Reference Comment
Deltar19.3kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar27.0cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M

phenoxide anion + Ethanol = C8H11O2-

By formula: C6H5O- + C2H6O = C8H11O2-

Quantity Value Units Method Reference Comment
Deltar19.3 ± 1.0kcal/molN/AMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar11.2 ± 1.6kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B

phenoxide anion + Water = (phenoxide anion bullet Water)

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

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Deltar15.4kcal/molPHPMSMeot-Ner and Sieck, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar23.9cal/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M

phenoxide anion + Water = C6H7O2-

By formula: C6H5O- + H2O = C6H7O2-

Quantity Value Units Method Reference Comment
Deltar15.4 ± 1.0kcal/molN/AMeot-Ner and Sieck, 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar8.2 ± 1.6kcal/molTDAsMeot-Ner and Sieck, 1986gas phase; B

Vibrational and/or electronic energy levels

Go To: Top, Reaction thermochemistry data, 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 by: Marilyn E. Jacox

State:   ?


 Energy 
 (cm-1
 Med.   Transition   «lambda»min 
 (nm) 
 «lambda»max 
 (nm) 
 References

Td = 18180 ± 50 gas Gunion, Gilles, et al., 1992

Additional references: Jacox, 1994, page 446

Notes

dPhotodissociation threshold

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Vibrational and/or electronic energy levels, 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]

Gunion, Gilles, et al., 1992
Gunion, R.F.; Gilles, M.K.; Polak, M.L.; Lineberger, W.C., Ultraviolet Photoelectron Spectroscopy of the Phenide, Benzyl, and Phenoxide Anions., Int. J. Mass Spectrom. Ion Proc., 1992, 117, 601, https://doi.org/10.1016/0168-1176(92)80115-H . [all data]

Jacox, 1994
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules, American Chemical Society, Washington, DC, 1994, 464. [all data]


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Vibrational and/or electronic energy levels, References