Phenol, 2-(1,1-dimethylethyl)-
- Formula: C10H14O
- Molecular weight: 150.2176
- IUPAC Standard InChIKey: WJQOZHYUIDYNHM-UHFFFAOYSA-N
- CAS Registry Number: 88-18-6
- 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, o-tert-butyl-; o-tert-Butylphenol; 2-tert-Butylphenol; 2-t-Butylphenol; Phenol, 2-tert-butyl-; 2-(1,1-Dimethylethyl)-phenol
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Phase change 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 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 | 497.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 497.06 | K | N/A | Tsvetkov, Nazmutdinov, et al., 1986 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 267.53 | K | N/A | McDonald, Shrader, et al., 1959 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 63.2 ± 0.2 | kJ/mol | N/A | Verevkin, 1999 | AC |
ΔvapH° | 77.03 | kJ/mol | C | Bertholon, Giray, et al., 1971 | ALS |
ΔvapH° | 80.9 | kJ/mol | N/A | Bertholon, Giray, et al., 1971 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
62.6 ± 0.2 | 309. | GS | Verevkin, 1999 | Based on data from 289. to 329. K.; AC |
74.1 | 424. | EB | Nesterova, Nazmutdinov, et al., 1990 | Based on data from 409. to 467. K.; AC |
54.9 | 368. | A | Stephenson and Malanowski, 1987 | Based on data from 353. to 498. K.; AC |
52.9 | 424. | N/A | Tsvetkov, Nazmutdinov, et al., 1986 | Based on data from 409. to 465. K.; AC |
55.6 | 348. | N/A | Stage, Müller, et al., 1953 | Based on data from 330. to 507. K.; AC |
53.9 | 373. | N/A | Stage, Müller, et al., 1953 | Based on data from 330. to 507. K.; AC |
51.0 | 423. | N/A | Stage, Müller, et al., 1953 | Based on data from 330. to 507. K.; AC |
47.0 | 473. | N/A | Stage, Müller, et al., 1953 | Based on data from 330. to 507. 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 |
---|---|---|---|---|
328.26 to 497.23 | 4.47765 | 1928.57 | -65.966 | McDonald, Shrader, et al., 1959, 2 |
Gas phase ion energetics data
Go To: Top, Phase change 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.10 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
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° | 1446. ± 9.2 | 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° | 1415. ± 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, Phase change 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.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Tsvetkov, Nazmutdinov, et al., 1986
Tsvetkov, V.S.; Nazmutdinov, A.G.; Sharonov, K.S.; Rozhnov, A.M.,
Termodin. Org. Soedin., 1986, 71. [all data]
McDonald, Shrader, et al., 1959
McDonald, R.A.; Shrader, S.A.; Stull, D.R.,
Vapor Pressures and Freezing Points of 30 Organics,
J. Chem. Eng. Data, 1959, 4, 311. [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]
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]
Nesterova, Nazmutdinov, et al., 1990
Nesterova, T.N.; Nazmutdinov, A.G.; Tsvetkov, V.S.; Rozhnov, A.M.; Roshchupkina, I. Yu,
Vapour pressures and enthalpies of vaporization of alkylphenols,
The Journal of Chemical Thermodynamics, 1990, 22, 4, 365-377, https://doi.org/10.1016/0021-9614(90)90122-7
. [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]
Stage, Müller, et al., 1953
Stage, H.; Müller, E.; Faldix, P.,
Erdol u Kohle, 1953, 6, 375. [all data]
McDonald, Shrader, et al., 1959, 2
McDonald, R.A.; Shrader, S.A.; Stull, D.R.,
Vapor Pressures and Freezing Points of Thirty Pure Organic Compounds.,
J. Chem. Eng. Data, 1959, 4, 4, 311-313, https://doi.org/10.1021/je60004a009
. [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]
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, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction 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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