Phenol, 2,4,6-tri-tert-butyl-
- Formula: C18H30O
- Molecular weight: 262.4302
- IUPAC Standard InChI: InChI=1S/C18H30O/c1-16(2,3)12-10-13(17(4,5)6)15(19)14(11-12)18(7,8)9/h10-11,19H,1-9H3
- IUPAC Standard InChIKey: PFEFOYRSMXVNEL-UHFFFAOYSA-N
- CAS Registry Number: 732-26-3
- 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, 2,4,6-tris(1,1-dimethylethyl)-; Alkofen B; P 23; 2,4,6-Tri-tert-butylphenol; 2,4,6-Tri-t-butylphenol; 2,4,6-Tri-tert-butyl-1-hydroxybenzene; 2,4,6-Tri-tert-butylhydroxybenzene; 2,4,6-Tris(1,1-dimethylethyl)phenol; 2,4,6-Tris(tert-butyl)phenol; NSC 14459; TM 02; Voidox
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -369.8 | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 |
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 | -498. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -10870. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | Corresponding ΔfHºsolid = -502. kJ/mol (simple calculation by NIST; no Washburn corrections) |
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.
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 551.2 | K | N/A | Weast and Grasselli, 1989 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 402.8 | K | N/A | Chickos, Braton, et al., 1991 | Uncertainty assigned by TRC = 1. K; TRC |
| Tfus | 405.7 | K | N/A | Inozemtsev, Liakumovich, et al., 1972 | Uncertainty assigned by TRC = 0.2 K; TRC |
| Tfus | 404. | K | N/A | Davies and Kybett, 1965 | Uncertainty assigned by TRC = 2.5 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 87.5 ± 0.4 | kJ/mol | GS | Verevkin, 1999 | AC |
| ΔsubH° | 128.1 | kJ/mol | C | Bertholon, Giray, et al., 1971 | ALS |
| ΔsubH° | 128.2 | kJ/mol | N/A | Bertholon, Giray, et al., 1971 | DRB |
| ΔsubH° | 85.60 ± 0.42 | kJ/mol | V | Davies and Kybett, 1965 | ALS |
| ΔsubH° | 84.2 ± 0.5 | kJ/mol | V | Aihara, 1960 | See also Verevkin, 1999.; AC |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 63.2 | 430. | A | Stephenson and Malanowski, 1987 | Based on data from 415. to 551. K.; AC |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 85.6 ± 0.4 | 317. | ME | Davies and Kybett, 1965 | Based on data from 295. to 339. K. See also Stephenson and Malanowski, 1987.; AC |
| 83.9 | 302. | N/A | Aihara, 1960 | Based on data from 292. to 313. K.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 19.46 | 405.2 | Chickos, Braton, et al., 1991, 2 | AC |
Entropy of fusion
| ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 21.66 | 405.2 | Chickos, Braton, et al., 1991 | CAL |
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 by: 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
+
=
+
By formula: C18H30O + C10H14O = C14H22O + C14H22O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 0.1 ± 0.46 | kJ/mol | Eqk | Pil'shchikov, Nesterova, et al., 1981 | liquid phase |
+
= 2
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 |
Gas phase ion energetics 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:
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 |
|---|---|---|---|
| 7.5 | PE | Cetinkaya, Lappert, et al., 1983 | LBLHLM |
| 7.82 | PE | Cetinkaya, Lappert, et al., 1983 | Vertical value; LBLHLM |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
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]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Chickos, Braton, et al., 1991
Chickos, J.S.; Braton, C.M.; Hesse, D.G.; Liebman, J.F.,
Estimating entropies and enthalpies of fusion of organic compounds,
J. Org. Chem., 1991, 56, 3, 927, https://doi.org/10.1021/jo00003a007
. [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]
Davies and Kybett, 1965
Davies, M.; Kybett, B.,
Sublimation and vaporization heats of long-chain alcohols,
Trans. Faraday Soc., 1965, 61, 1608. [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]
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]
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]
Chickos, Braton, et al., 1991, 2
Chickos, James S.; Braton, C. Marie; Hesse, Donald G.; Liebman, Joel F.,
Estimating entropies and enthalpies of fusion of organic compounds,
J. Org. Chem., 1991, 56, 3, 927-938, https://doi.org/10.1021/jo00003a007
. [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]
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, 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 ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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