Benzene, 1,3,5-tri-tert-butyl-
- Formula: C18H30
- Molecular weight: 246.4308
- IUPAC Standard InChIKey: GUFMBISUSZUUCB-UHFFFAOYSA-N
- CAS Registry Number: 1460-02-2
- 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: Benzene, 1,3,5-tris(1,1-dimethylethyl)-; 1,3,5-Tri-tert-butylbenzene; 1,3,5-Tris-(1,1-dimethylethyl)benzene; 1,3,5-Tri-t-butylbenzene
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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°liquid | -73.32 ± 0.56 | kcal/mol | Eqk | Nesterova, Verevkin, et al., 1984 | GLC |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2640.7 ± 0.9 | kcal/mol | Cm | Kruerke, Hoogzand, et al., 1961 | Corresponding ΔfHºsolid = -76.9 kcal/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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 521.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 345.05 | K | N/A | Arnett, Sanda, et al., 1967 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 346.3 | K | N/A | Davies and Kybett, 1965 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 346.8 | K | N/A | Ogimachi, Andrews, et al., 1955 | Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 19.4 ± 0.07 | kcal/mol | N/A | Verevkin, 1998 | AC |
ΔsubH° | 19.06 ± 0.09 | kcal/mol | V | Davies and Kybett, 1965 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
394.7 | 0.016 | Weast and Grasselli, 1989 | BS |
401. to 403. | 0.024 | Frinton Laboratories Inc., 1986 | BS |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
19.1 ± 0.07 | 319. | T | Verevkin, 1998 | Based on data from 298. to 341. K.; AC |
19.0 ± 0.1 | 294. | ME | Davies and Kybett, 1965 | Based on data from 273. to 315. K. See also Stephenson and Malanowski, 1987.; AC |
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: C18H30 + C10H14 = C14H22 + C14H22
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 0.24 ± 0.26 | kcal/mol | Eqk | Nesterova, Verevkin, et al., 1984 | liquid phase; GLC |
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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 202.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 196.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.56 ± 0.07 | EI | Arnett, Sanda, et al., 1967 | RDSH |
8.19 | PE | Howell, Goncalves, et al., 1984 | Vertical value; LBLHLM |
8.46 | PE | Cetinkaya, Lappert, et al., 1983 | Vertical value; LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C17H27+ | 11.91 ± 0.07 | CH3 | EI | Arnett, Sanda, et al., 1967 | RDSH |
IR Spectrum
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | SRD/NIST Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | EPA-IR VAPOR PHASE LIBRARY |
State | gas |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Nesterova, Verevkin, et al., 1984
Nesterova, T.N.; Verevkin, S.R.; Karaseva, S.Ya.; Rozhnov, A.M.; Tsvetkov, V.F.,
The equilibria in the interconversions of t-butylbenzenes,
Russ. J. Phys. Chem. (Engl. Transl.), 1984, 58, 297-298. [all data]
Kruerke, Hoogzand, et al., 1961
Kruerke, U.; Hoogzand, C.; Hubel, W.,
Uber organometall-komplexe, VI 1.2.4-tri-tert.-butyl-benzol,
Chem. Ber., 1961, 94, 2817-2820. [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]
Arnett, Sanda, et al., 1967
Arnett, E.M.; Sanda, J.C.; Bollinger, J.M.; Barber, M.,
Crowded benzenes. VI. The strain energy in o-di-tbutylbenzenes,
J. Am. Chem. Soc., 1967, 89, 5389. [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]
Ogimachi, Andrews, et al., 1955
Ogimachi, N.N.; Andrews, L.J.; Keefer, R.M.,
The Free Energies and Heats of Formation of Polyalkoxybenzene-Iodine Monochloride Complexes,
J. Am. Chem. Soc., 1955, 77, 4202. [all data]
Verevkin, 1998
Verevkin, Sergey P.,
Thermochemical properties of branched alkylsubstituted benzenes,
The Journal of Chemical Thermodynamics, 1998, 30, 8, 1029-1040, https://doi.org/10.1006/jcht.1998.0370
. [all data]
Frinton Laboratories Inc., 1986
Frinton Laboratories Inc.,
Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Howell, Goncalves, et al., 1984
Howell, J.O.; Goncalves, J.M.; Amatore, C.; Klasinc, L.; Wightman, R.M.; Kochi, J.K.,
Electron transfer from aromatic hydrocarbons and their π-complexes with metals. Comparison of the standard oxidation potentials and vertical ionization potentials,
J. Am. Chem. Soc., 1984, 106, 3968. [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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