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Reaction data

phenoxide anion + Hydrogen cation = Phenol


Enthalpy of reaction at standard conditions (nominally 298.15 K, 1 atm.)

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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

DeltarH° (kJ/mol) Method Reference Comment
1456. ± 4.2CIDCAngel and Ervin, 2006gas phase; B
1467.7 ± 3.7D-EAGunion, Gilles, et al., 1992gas phase; Derived BDE from D-EA cycle: 87.6±2.2 kcal/mol; B
1461. ± 8.8G+TSBartmess, 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
1454. ± 7.9CIDCAngel and Ervin, 2004gas phase; B
1466. ± 13.EndoDeTuri and Ervin, 1998gas phase; Re-analyzed (private comm., KME): acidity strengthened by 1.2 kcal/mol from value in paper. BDE now 88.7 kcal/mol; B
1466. ± 9.6G+TSCumming and Kebarle, 1978gas phase; B
>1457. ± 7.1D-EARichardson, Stephenson, et al., 1975gas phase; B; Data excluded from overall average

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Angel and Ervin, 2006
Angel, L.A.; Ervin, K.M., Gas-phase acidities and O-H bond dissociation enthalpies of phenol, 3-methylphenol, 2,4,6-trimethylphenol, and ethanoic acid, J. Phys. Chem. A, 2006, 110, 35, 10392-10403, https://doi.org/10.1021/jp0627426 . [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]

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]

DeTuri and Ervin, 1998
DeTuri, V.F.; Ervin, K.M., Proton transfer between Cl- and C6H5OH. O-H bond energy of phenol, Int. J. Mass Spectrom., 1998, 175, 1-2, 123-132, https://doi.org/10.1016/S0168-1176(98)00112-8 . [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]


Notes

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