Phenol, p-tert-butyl-
- Formula: C10H14O
- Molecular weight: 150.2176
- 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
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -186.2 | kJ/mol | Eqk | Verevkin, 1982 | Isomerization; ALS |
ΔfH°gas | -214.8 | kJ/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 | -174.3 | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | ALS |
Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -310.5 ± 1.2 | kJ/mol | Ccb | Ammar, El Sayed, et al., 1977 | |
ΔfH°solid | -270. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -5625.8 ± 1.2 | kJ/mol | Ccb | Ammar, El Sayed, et al., 1977 | Corresponding ΔfHºsolid = -310.1 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -5669. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | Corresponding ΔfHºsolid = -270. kJ/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 507. ± 10. | K | AVG | N/A | Average of 11 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 372. ± 2. | K | AVG | N/A | Average of 32 out of 33 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 67.9 ± 1.0 | kJ/mol | C | Ribeiro da Silva, Matos, et al., 1999 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 89.4 ± 2.5 | kJ/mol | C | Ribeiro da Silva, Matos, et al., 1999 | AC |
ΔsubH° | 85.9 ± 0.5 | kJ/mol | GS | Verevkin, 1999 | Based on data from 293. to 334. K.; AC |
ΔsubH° | 93.43 | kJ/mol | C | Bertholon, Giray, et al., 1971 | ALS |
ΔsubH° | 95.7 | kJ/mol | N/A | Bertholon, Giray, et al., 1971 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
54.3 | 486. | A,GS,EB | Stephenson and Malanowski, 1987 | Based on data from 471. to 525. K. See also Stull, 1947 and Handley, Harrop, et al., 1964.; AC |
59.6 | 348. | N/A | Stage, Müller, et al., 1953 | Based on data from 346. to 523. K.; AC |
57.6 | 373. | N/A | Stage, Müller, et al., 1953 | Based on data from 346. to 523. K.; AC |
56.6 | 398. | N/A | Stage, Müller, et al., 1953 | Based on data from 346. to 523. K.; AC |
54.4 | 423. | N/A | Stage, Müller, et al., 1953 | Based on data from 346. to 523. K.; AC |
49.9 | 473. | N/A | Stage, Müller, et al., 1953 | Based on data from 346. to 523. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
471.27 to 524.8 | 4.11825 | 1622.037 | -118.559 | Handley, Harrop, et al., 1964, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
85.0 ± 0.5 | 313. | GS | Verevkin, 1999 | Based on data from 293. to 334. K.; AC |
84.3 | 292. | A | Stephenson and Malanowski, 1987 | Based on data from 280. to 304. K. See also Aihara, 1960.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.52 | 373.2 | Inozemtsev, Liakumovich, et al., 1972 | AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
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° | 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° | 1429. ± 8.4 | kJ/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° | -1.0 | kJ/mol | Eqk | Verevkin, 1982 | gas phase; Isomerization; ALS |
ΔrH° | -1. ± 1.3 | kJ/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
By formula: C6H6O + C14H22O = C10H14O + C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 0.08 ± 0.71 | kJ/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. ± 4. | kJ/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
By formula: C18H30O + C10H14O = 2C14H22O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -12.4 ± 2.0 | kJ/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
By formula: C10H14O = C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 18.6 ± 0.79 | kJ/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase; ALS |
By formula: C10H14O = C10H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -16.9 ± 1.6 | kJ/mol | Eqk | Nesterova, Verevkin, et al., 1985 | liquid phase; ALS |
By formula: C10H14O = C6H6O + C4H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 71.0 ± 2.1 | kJ/mol | Eqk | Verevkin, 1982 | gas phase; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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° | 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° | 1429. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-1815 |
NIST MS number | 228357 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]
Ribeiro da Silva, Matos, et al., 1999
Ribeiro da Silva, M.A.V.; Matos, M.A.R.; Morais, V.M.F.; Miranda, M.S.,
Thermochemical and Theoretical Study of tert -Butyl and Di- tert -butylphenol Isomers,
J. Org. Chem., 1999, 64, 24, 8816-8820, https://doi.org/10.1021/jo990801o
. [all data]
Verevkin, 1999
Verevkin, S.P.,
Thermochemistry of phenols: quantification of theortho-,para-, andmeta-interactions in tert-alkyl substituted phenols,
The Journal of Chemical Thermodynamics, 1999, 31, 5, 559-585, https://doi.org/10.1006/jcht.1998.0459
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Handley, Harrop, et al., 1964
Handley, R.; Harrop, D.; Martin, J.F.; Sprake, C.H.S.,
846. Thermodynamic properties of organic oxygen compounds. Part XIV. Purification and vapour pressures of some alkylphenols,
J. Chem. Soc., 1964, 4404, https://doi.org/10.1039/jr9640004404
. [all data]
Stage, Müller, et al., 1953
Stage, H.; Müller, E.; Faldix, P.,
Erdol u Kohle, 1953, 6, 375. [all data]
Handley, Harrop, et al., 1964, 2
Handley, R.; Harrop, D.; Martin, J.F.; Sprake, C.H.S.,
Thermodynamic Properties of Organic Oxygen Compounds. Part XIV. Purification and Vapour Pressures of Some Alkylphenols,
J. Chem. Soc., 1964, 4404-4406, https://doi.org/10.1039/jr9640004404
. [all data]
Aihara, 1960
Aihara, Ariyuki,
Estimation of the Energy of Hydrogen Bonds Formed in Crystals. II. Phenols,
Bull. Chem. Soc. Jpn., 1960, 33, 2, 194-200, https://doi.org/10.1246/bcsj.33.194
. [all data]
Inozemtsev, Liakumovich, et al., 1972
Inozemtsev, P.P.; Liakumovich, A.G.; Gracheva, Z.D.,
Russ. J. Phys. Chem., 1972, 46, 6, 914. [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point 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 ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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