phenoxide anion
- Formula: C6H5O-
- Molecular weight: 93.1038
- IUPAC Standard InChI: InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H/p-1
- IUPAC Standard InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-M
- CAS Registry Number: 3229-70-7
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Gas phase ion energetics 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 by: John E. Bartmess
Protonation 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 |
| ΔrG° | 1426. ± 7.9 | kJ/mol | CIDC | Angel and Ervin, 2004 | gas phase |
| ΔrG° | 1437. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase |
| ΔrG° | >1429. ± 7.5 | kJ/mol | H-TS | Richardson, Stephenson, et al., 1975 | gas phase |
References
Go To: Top, 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]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.