Phenol, m-tert-butyl-
- Formula: C10H14O
- Molecular weight: 150.2176
- IUPAC Standard InChI: InChI=1S/C10H14O/c1-10(2,3)8-5-4-6-9(11)7-8/h4-7,11H,1-3H3
- IUPAC Standard InChIKey: CYEKUDPFXBLGHH-UHFFFAOYSA-N
- CAS Registry Number: 585-34-2
- 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: Phenol, 3-(1,1-dimethylethyl)-; m-tert-Butylphenol; 3-tert-Butylphenol; 3-t-Butylphenol; Phenol, 3-tert-butyl-
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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 | -185.2 | kJ/mol | Eqk | Verevkin, 1982 | |
| ΔfH°gas | -184. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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°solid | -280. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -5661. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | Corresponding ΔfHºsolid = -280. kJ/mol (simple calculation by NIST; no Washburn corrections) |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed 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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.40 | PE | Cetinkaya, Lappert, et al., 1983 | Vertical value; LBLHLM |
De-protonation reactions
C10H13O- + =
By formula: C10H13O- + H+ = C10H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1458. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1430. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed 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.
Verevkin, 1982
Verevkin, S.P.,
Study of equilibrium of tert-butylphenol dealkylation in the gas phase,
Termodin. Organ. Soedin., 1982, 67-70. [all data]
Bertholon, Giray, et al., 1971
Bertholon, G.; Giray, M.; Perrin, R.; Vincent-Falquet-Berny, M.F.,
No. 532. - Etude physicochimique des phenols. OX. - Ethanlpies de combustion et energies de resonance des alcoyl et aryphenols,
Bull. Soc. Chim. France, 1971, 3180-3187. [all data]
Cetinkaya, Lappert, et al., 1983
Cetinkaya, B.; Lappert, M.F.; Suffolk, R.J.,
Photoelectron spectra of some sterically hindered phenols and related compounds,
J. Chem. Res. Synop., 1983, 316. [all data]
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid 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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