Phenol, p-tert-butyl-
- Formula: C10H14O
- Molecular weight: 150.2176
- IUPAC Standard InChI: InChI=1S/C10H14O/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7,11H,1-3H3
- IUPAC Standard InChIKey: QHPQWRBYOIRBIT-UHFFFAOYSA-N
- CAS Registry Number: 98-54-4
- 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, 4-(1,1-dimethylethyl)-; p-tert-Butylphenol; Butylphen; 4-tert-Butylphenol; 4-t-Butylphenol; 4-(1,1-Dimethylethyl)phenol; p-terc.Butylfenol; 1-Hydroxy-4-tert-butylbenzene; PTBP; Phenol, 4-tert-butyl-; p-t-Butylphenol; NSC 3697
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Gas phase thermochemistry data
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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -44.50 | kcal/mol | Eqk | Verevkin, 1982 | Isomerization; ALS |
| ΔfH°gas | -51.34 | kcal/mol | N/A | Ammar, El Sayed, et al., 1977 | Value computed using ΔfHsolid° value of -310.5±1.2 kj/mol from Ammar, El Sayed, et al., 1977 and ΔsubH° value of 95.7 kj/mol from Bertholon, Giray, et al., 1971.; DRB |
| ΔfH°gas | -41.67 | kcal/mol | Ccb | Bertholon, Giray, et al., 1971 | ALS |
Reaction thermochemistry data
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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C10H13O- + =
By formula: C10H13O- + H+ = C10H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 348.5 ± 2.1 | kcal/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° | 341.6 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
=
By formula: C10H14O = C10H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -0.24 | kcal/mol | Eqk | Verevkin, 1982 | gas phase; Isomerization; ALS |
| ΔrH° | -0.23 ± 0.32 | kcal/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
+
=
+
By formula: C6H6O + C14H22O = C10H14O + C10H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 0.02 ± 0.17 | kcal/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
+
=
+
By formula: C6H6O + C14H22O = C10H14O + C10H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -0.0 ± 0.9 | kcal/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
+
= 2
By formula: C18H30O + C10H14O = 2C14H22O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -2.96 ± 0.47 | kcal/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
=
By formula: C10H14O = C10H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 4.44 ± 0.19 | kcal/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
=
By formula: C10H14O = C10H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -4.04 ± 0.38 | kcal/mol | Eqk | Nesterova, Verevkin, et al., 1985 | liquid phase; ALS |
=
+
By formula: C10H14O = C6H6O + C4H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 17.0 ± 0.50 | kcal/mol | Eqk | Verevkin, 1982 | gas phase; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction 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 |
|---|---|---|---|
| 7.8 | PE | Cetinkaya, Lappert, et al., 1983 | LBLHLM |
| 8.16 | 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° | 348.5 ± 2.1 | kcal/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° | 341.6 ± 2.0 | kcal/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, Reaction 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]
Ammar, El Sayed, et al., 1977
Ammar, M.M.; El Sayed, N.; Morsi, S.E.; El Azmirly, A.,
The enthalpies of combustion and formation of p-tertiary butyl phenol and naphthalene,
Egypt. J. Phys., 1977, 8, 111-118. [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]
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]
Pil'shchikov, Nesterova, et al., 1981
Pil'shchikov, V.A.; Nesterova, T.N.; Rozhnov, A.M.,
Equilibrium in the system phenol-tert-butylphenols,
J. Appl. Chem. USSR, 1981, 54, 1765-1769. [all data]
Nesterova, Verevkin, et al., 1985
Nesterova, T.N.; Verevkin, S.P.; Malova, T.N.; Pilshchikov, V.A.,
Study of an equilibrium of tert-alkylphenols (thermodynamic analysis of the alkylation of phenols by branched olefins),
Zh. Prikl. Khim. (Leningrad), 1985, 58, 827-833. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction 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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