phenoxide anion
- Formula: C6H5O-
- Molecular weight: 93.1038
- IUPAC Standard InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-M
- CAS Registry Number: 3229-70-7
- Chemical structure:
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Reaction thermochemistry data
Go To: Top, 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
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Individual Reactions
By formula: C6H5O- + H+ = C6H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1462. ± 10. | kJ/mol | AVG | N/A | Average of 6 out of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1432. ± 8.4 | kJ/mol | IMRE | 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 |
ΔrG° | 1426. ± 7.9 | kJ/mol | CIDC | Angel and Ervin, 2004 | gas phase; B |
ΔrG° | 1437. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
ΔrG° | >1429. ± 7.5 | kJ/mol | H-TS | Richardson, Stephenson, et al., 1975 | gas phase; B |
By formula: C6H5O- + C2H4O2 = (C6H5O- • C2H4O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 115. | kJ/mol | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; calculated from CH3COO-.C6H5OH; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 100. | J/mol*K | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; calculated from CH3COO-.C6H5OH; M |
By formula: C6H5O- + H2O = (C6H5O- • H2O)
Bond type: Hydrogen bond (negative ion to hydride)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 64.4 | kJ/mol | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 100. | J/mol*K | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
+ = C6H7O2-
By formula: C6H5O- + H2O = C6H7O2-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 64.4 ± 4.2 | kJ/mol | N/A | Meot-Ner and Sieck, 1986 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 34. ± 6.7 | kJ/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
+ = C8H11O2-
By formula: C6H5O- + C2H6O = C8H11O2-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 80.8 ± 4.2 | kJ/mol | N/A | Meot-Ner and Sieck, 1986 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 46.9 ± 6.7 | kJ/mol | TDAs | Meot-Ner and Sieck, 1986 | gas phase; B |
By formula: C6H5O- + C2H6O = (C6H5O- • C2H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 80.8 | kJ/mol | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 113. | J/mol*K | PHPMS | Meot-Ner and Sieck, 1986 | gas phase; M |
References
Go To: Top, Reaction thermochemistry 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
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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