Phenol, pentafluoro-
- Formula: C6HF5O
- Molecular weight: 184.0636
- IUPAC Standard InChI: InChI=1S/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
- IUPAC Standard InChIKey: XBNGYFFABRKICK-UHFFFAOYSA-N
- CAS Registry Number: 771-61-9
- 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. - Other names: Pentafluorophenol; C6F5OH; 2,3,4,5,6-Pentafluorophenol
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Gas phase thermochemistry data
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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -957.1 ± 2.0 | kJ/mol | Ccr | Cox, Gundry, et al., 1969 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry 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 as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.20 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
| 9.37 ± 0.02 | PE | Maier, Marthaler, et al., 1980 | Vertical value; LLK |
De-protonation reactions
C6F5O- + =
By formula: C6F5O- + H+ = C6HF5O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1372. ± 9.2 | kJ/mol | G+TS | Koppel, Taft, et al., 1994 | gas phase; B |
| ΔrH° | <1630. ± 11. | kJ/mol | Acid | Briscese and Riveros, 1975 | gas phase; HO- + C6F6 -> , acidity probably ca. 320 kcal; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1342. ± 8.4 | kJ/mol | IMRE | Koppel, Taft, et al., 1994 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, 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.
Cox, Gundry, et al., 1969
Cox, J.D.; Gundry, H.A.; Harrop, D.; Head, A.J.,
Thermodynamic properties of fluorine compounds. 9. Enthalpies of formation of some compounds containing the pentafluorophenyl group,
J. Chem. Thermodyn., 1969, 1, 77-87. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]
Maier, Marthaler, et al., 1980
Maier, J.P.; Marthaler, O.; Mohraz, M.,
Emission spectra of the cations of some fluorosubstituted phenols in the gaseous phase,
J. Electron Spectrosc. Relat. Phenom., 1980, 19, 11. [all data]
Koppel, Taft, et al., 1994
Koppel, I.A.; Taft, R.W.; Anvia, F.; Zhu, S.Z.; Hu, L.Q.; Sung, K.S.; Desmarteau, D.D.; Yagupolskii, L.M.,
The Gas-Phase Acidities of Very Strong Neutral Bronsted Acids,
J. Am. Chem. Soc., 1994, 116, 7, 3047, https://doi.org/10.1021/ja00086a038
. [all data]
Briscese and Riveros, 1975
Briscese, S.M.J.; Riveros, J.M.,
Gas phase nucleophilic reactions of aromatic systems,
J. Am. Chem. Soc., 1975, 97, 230. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions 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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