Benzene, 1,4-bis(1,1-dimethylethyl)-
- Formula: C14H22
- Molecular weight: 190.3245
- IUPAC Standard InChIKey: OOWNNCMFKFBNOF-UHFFFAOYSA-N
- CAS Registry Number: 1012-72-2
- 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, p-di-tert-butyl-; p-Di-tert-butylbenzene; 1,4-Di-tert-butylbenzene; Benzene, 1,4-bis-(tert-butyl)
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Phase change data
Go To: Top, 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 508.15 | K | N/A | Malishev, 1935 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 351. ± 6. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 350.8 | K | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 708. | K | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 2. K; derived from fit of obs. vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 22.70 | atm | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 1.97 atm; derived from fit of obs. vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 1.37 | mol/l | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 0.079 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 15.1 ± 0.02 | kcal/mol | EB,IP | Chirico and Steele, 2009 | Based on data from 319. to 559. K.; AC |
ΔvapH° | 14.7 ± 0.07 | kcal/mol | GS | Verevkin, Kozlova, et al., 2008 | Based on data from 354. to 382. K.; AC |
ΔvapH° | 15.1 ± 0.1 | kcal/mol | EB | Steele, Chirico, et al., 1997, 2 | Based on data from 387. to 559. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 19.8 ± 0.1 | kcal/mol | N/A | Verevkin, 1998 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.3 ± 0.02 | 360. | EB,IP | Chirico and Steele, 2009 | Based on data from 319. to 559. K.; AC |
13.0 ± 0.02 | 400. | EB,IP | Chirico and Steele, 2009 | Based on data from 319. to 559. K.; AC |
14.7 ± 0.02 | 440. | EB,IP | Chirico and Steele, 2009 | Based on data from 319. to 559. K.; AC |
11.1 ± 0.05 | 480. | EB,IP | Chirico and Steele, 2009 | Based on data from 319. to 559. K.; AC |
10.7 ± 0.07 | 520. | EB,IP[ | Chirico and Steele, 2009 | Based on data from 319. to 559. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
19.6 ± 0.1 | 310. | T | Verevkin, 1998 | Based on data from 288. to 333. K.; AC |
19.8 | 305. | ME | Hopke and Sears, 1951 | Based on data from 285. to 325. K. See also Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
2.0 | 350.8 | AC,DSC | Chirico and Steele, 2009 | AC |
5.373 | 341.5 | N/A | Steele, Chirico, et al., 1997, 2 | AC |
Reaction 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
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 |
By formula: C14H22 = C14H22
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 0.354 ± 0.079 | kcal/mol | Eqk | Nesterova, Verevkin, et al., 1984 | liquid phase; GLC |
Gas phase ion energetics data
Go To: Top, Phase change data, Reaction thermochemistry 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.24 ± 0.02 | EI | Orlov, Misharev, et al., 1986 | LBLHLM |
8.11 | PE | Baidin, Misharev, et al., 1985 | LBLHLM |
8.30 | PE | Bock, Kaim, et al., 1978 | LLK |
8.74 ± 0.07 | EI | Arnett, Sanda, et al., 1967 | RDSH |
8.31 | PE | Baidin, Misharev, et al., 1985 | Vertical value; LBLHLM |
8.28 | PE | Howell, Goncalves, et al., 1984 | Vertical value; LBLHLM |
8.40 | PE | Kaim, Tesmann, et al., 1980 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C13H19+ | 9.5 ± 0.1 | CH3 | EI | Orlov, Misharev, et al., 1986 | LBLHLM |
C13H19+ | 11.69 ± 0.07 | CH3 | EI | Arnett, Sanda, et al., 1967 | RDSH |
References
Go To: Top, 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.
Malishev, 1935
Malishev, B.W.,
Direct Alkylation of Aromatic Hydrocarbons by Olefins Under Catalytic Influence of Phosphorous Pentoxide,
J. Am. Chem. Soc., 1935, 57, 883. [all data]
Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor Pressure, Heat Capacity, and Density along the Saturted Line, Measurements for Cyclohexanol, 2-Cyclohexen-1-one, 1,2-Dichloropropane, 1,4-Di-tert-butylbenzene, (±)-2-Ethylhexanoic Acid, 1-(m,
J. Chem. Eng. Data, 1997, 42, 1021-36. [all data]
Chirico and Steele, 2009
Chirico, Robert D.; Steele, William V.,
Thermodynamic properties of tert-butylbenzene and 1,4-di-tert-butylbenzene,
The Journal of Chemical Thermodynamics, 2009, 41, 3, 392-401, https://doi.org/10.1016/j.jct.2008.10.008
. [all data]
Verevkin, Kozlova, et al., 2008
Verevkin, Sergey P.; Kozlova, Svetlana A.; Emel'yanenko, Vladimir N.; Goodrich, Peter; Hardacre, Christopher,
Thermochemistry of Ionic Liquid-Catalyzed Reactions. Experimental and Theoretical Study of Chemical Equilibria of Isomerization and Transalkylation of tert -Butylbenzenes,
J. Phys. Chem. A, 2008, 112, 44, 11273-11282, https://doi.org/10.1021/jp806410x
. [all data]
Steele, Chirico, et al., 1997, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor Pressure, Heat Capacity, and Density along the Saturation Line, Measurements for Cyclohexanol, 2-Cyclohexen-1-one, 1,2-Dichloropropane, 1,4-Di- tert -butylbenzene, (±)-2-Ethylhexanoic Acid, 2-(Methylamino)ethanol, Perfluoro- n -heptane, and Sulfolane,
J. Chem. Eng. Data, 1997, 42, 6, 1021-1036, https://doi.org/10.1021/je9701036
. [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]
Hopke and Sears, 1951
Hopke, E.R.; Sears, G.W.,
Vapor Pressures below 1 mm Hg of Several Aromatic Compounds,
J. Chem. Phys., 1951, 19, 11, 1345, https://doi.org/10.1063/1.1748057
. [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]
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]
Orlov, Misharev, et al., 1986
Orlov, V.; Misharev, A.; Takhistox, V.,
Determination of the enthalpy of formation of para-substituted α,α-dimethyl cations in the gas phase,
Izv. Akad. Nauk SSSR Ser. Khim., 1986, 9, 2006. [all data]
Baidin, Misharev, et al., 1985
Baidin, V.N.; Misharev, A.D.; Takhistov, V.V.,
Effect of alkyl substituents on the ionization potentials of halogenobenzenes,
Zh. Org. Khim., 1985, 21, 817. [all data]
Bock, Kaim, et al., 1978
Bock, H.; Kaim, W.; Rohwer, H.E.,
Die hyperkonjugative Stabilisierung von p-Xylol-Radikalkationen durch (H3C)3Si-Substituenten,
Chem. Ber., 1978, 111, 3573. [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]
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]
Kaim, Tesmann, et al., 1980
Kaim, W.; Tesmann, H.; Bock, H.,
Me3C-, Me3Si-, Me3Ge-, Me3Sn- und Me3Pb-substituierte benzol- und naphthalin-derivate und ihre radikalanionen,
Chem. Ber., 1980, 113, 3221. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion 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 ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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