Phenol, 2,6-bis(1,1-dimethylethyl)-
- Formula: C14H22O
- Molecular weight: 206.3239
- IUPAC Standard InChIKey: DKCPKDPYUFEZCP-UHFFFAOYSA-N
- CAS Registry Number: 128-39-2
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Phenol, 2,6-di-tert-butyl-; 2,6-Bis(tert-butyl)phenol; 2,6-Bis(1,1-dimethylethyl)phenol; 2,6-Di-tert-butylphenol; Phenol, 2,6-bis(t-butyl); 2,6-di-t-Butylphenol; Ethanox 701; Ethyl 701; 2,6-DTBP; 2,6-(1,1-Dimethylethyl)phenol; 2,6-Bis(t-butyl)phenol; Isonox 103; AN 701; Ethyl AN 701; Hitec 4701; NSC 49175; Phenol, 2,4-di-tert.-butyl
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Gas phase thermochemistry data
Go To: Top, Phase change 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 | -62.5 | kcal/mol | Ccb | Bertholon, Giray, et al., 1971 |
Phase change 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:
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 | 526.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 311. | K | N/A | Inozemtsev, Liakumovich, et al., 1972 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 310.5 | K | N/A | Thomas and Meatyard, 1963 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 15.8 ± 0.05 | kcal/mol | N/A | Verevkin, 1999 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 19.5 ± 0.55 | kcal/mol | C | Ribeiro da Silva, Matos, et al., 1999 | AC |
ΔsubH° | 20.2 ± 0.1 | kcal/mol | GS | Verevkin, 1999 | AC |
ΔsubH° | 26.50 | kcal/mol | C | Bertholon, Giray, et al., 1971 | ALS |
ΔsubH° | 25.81 | kcal/mol | N/A | Bertholon, Giray, et al., 1971 | DRB |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.2 ± 0.05 | 341. | GS | Verevkin, 1999 | Based on data from 313. to 368. K.; AC |
14.4 | 401. | A | Stephenson and Malanowski, 1987 | Based on data from 386. to 530. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.960 | 310.7 | Inozemtsev, Liakumovich, et al., 1972 | AC |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, 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:
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 |
---|---|---|---|
7.70 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
8.15 | PE | Cetinkaya, Lappert, et al., 1983 | Vertical value; LBLHLM |
References
Go To: Top, Gas phase thermochemistry data, 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.
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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Thomas and Meatyard, 1963
Thomas, L.H.; Meatyard, R.,
Viscosity and Molecular Association. IV. Association of Monohydric Alcohols and Some Hindered Phenols.,
J. Chem. Soc., 1963, 1963, 1986-2002. [all data]
Verevkin, 1999
Verevkin, Sergey P.,
Thermochemistry of phenols: buttress effects in sterically hindered phenols,
The Journal of Chemical Thermodynamics, 1999, 31, 11, 1397-1416, https://doi.org/10.1006/jcht.1999.0466
. [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]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion 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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