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
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Gas phase ion energetics data
Go To: Top, 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
+
=
By formula: C6H5O- + H+ = C6H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 349. ± 2. | kcal/mol | AVG | N/A | Average of 6 out of 7 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 342.3 ± 2.0 | kcal/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° | 340.8 ± 1.9 | kcal/mol | CIDC | Angel and Ervin, 2004 | gas phase |
| ΔrG° | 343.4 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase |
| ΔrG° | >341.5 ± 1.8 | kcal/mol | H-TS | Richardson, Stephenson, et al., 1975 | gas phase |
Vibrational and/or electronic energy levels
Go To: Top, Gas phase ion energetics 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 | λmin (nm) |
λmax (nm) |
References | ||
|---|---|---|---|---|---|---|---|
| Td = 18180 ± 50 | gas | Gunion, Gilles, et al., 1992 | |||||
Additional references: Jacox, 1994, page 446
Notes
| d | Photodissociation threshold |
References
Go To: Top, Gas phase ion energetics 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]
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, Gas phase ion energetics data, Vibrational and/or electronic energy levels, 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
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