Reaction data
+ =
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
ΔrH° (kJ/mol) | Method | Reference | Comment |
---|---|---|---|
1456. ± 4.2 | CIDC | Angel and Ervin, 2006 | gas phase; B |
1467.7 ± 3.7 | D-EA | Gunion, Gilles, et al., 1992 | gas phase; Derived BDE from D-EA cycle: 87.6±2.2 kcal/mol; B |
1461. ± 8.8 | G+TS | Bartmess, Scott, et al., 1979 | gas 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 |
1454. ± 7.9 | CIDC | Angel and Ervin, 2004 | gas phase; B |
1466. ± 13. | Endo | DeTuri and Ervin, 1998 | gas 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. ± 9.6 | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
>1457. ± 7.1 | D-EA | Richardson, Stephenson, et al., 1975 | gas phase; B; Data excluded from overall average |
References
Go To: Top, Enthalpy of reaction at standard conditions (nominally 298.15 K, 1 atm.), Notes
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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- Symbols used in this document:
ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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