Benzene, 1,4-bis(1,1-dimethylethyl)-

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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil508.15KN/AMalishev, 1935Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Tfus351. ± 6.KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple350.8KN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tc708.KN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 2. K; derived from fit of obs. vapor pressure; TRC
Quantity Value Units Method Reference Comment
Pc22.70atmN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 1.97 atm; derived from fit of obs. vapor pressure; TRC
Quantity Value Units Method Reference Comment
ρc1.37mol/lN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 0.079 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap15.1 ± 0.02kcal/molEB,IPChirico and Steele, 2009Based on data from 319. to 559. K.; AC
Δvap14.7 ± 0.07kcal/molGSVerevkin, Kozlova, et al., 2008Based on data from 354. to 382. K.; AC
Δvap15.1 ± 0.1kcal/molEBSteele, Chirico, et al., 1997, 2Based on data from 387. to 559. K.; AC
Quantity Value Units Method Reference Comment
Δsub19.8 ± 0.1kcal/molN/AVerevkin, 1998AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
13.3 ± 0.02360.EB,IPChirico and Steele, 2009Based on data from 319. to 559. K.; AC
13.0 ± 0.02400.EB,IPChirico and Steele, 2009Based on data from 319. to 559. K.; AC
14.7 ± 0.02440.EB,IPChirico and Steele, 2009Based on data from 319. to 559. K.; AC
11.1 ± 0.05480.EB,IPChirico and Steele, 2009Based on data from 319. to 559. K.; AC
10.7 ± 0.07520.EB,IP[Chirico and Steele, 2009Based on data from 319. to 559. K.; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
19.6 ± 0.1310.TVerevkin, 1998Based on data from 288. to 333. K.; AC
19.8305.MEHopke and Sears, 1951Based 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
2.0350.8AC,DSCChirico and Steele, 2009AC
5.373341.5N/ASteele, Chirico, et al., 1997, 2AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

Benzene, 1,3,5-tri-tert-butyl- + Benzene, tert-butyl- = Benzene, 1,4-bis(1,1-dimethylethyl)- + Benzene, 1,3-bis(1,1-dimethylethyl)-

By formula: C18H30 + C10H14 = C14H22 + C14H22

Quantity Value Units Method Reference Comment
Δr0.24 ± 0.26kcal/molEqkNesterova, Verevkin, et al., 1984liquid phase; GLC

Benzene, 1,4-bis(1,1-dimethylethyl)- = Benzene, 1,3-bis(1,1-dimethylethyl)-

By formula: C14H22 = C14H22

Quantity Value Units Method Reference Comment
Δr0.354 ± 0.079kcal/molEqkNesterova, Verevkin, et al., 1984liquid 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 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 ± 0.02EIOrlov, Misharev, et al., 1986LBLHLM
8.11PEBaidin, Misharev, et al., 1985LBLHLM
8.30PEBock, Kaim, et al., 1978LLK
8.74 ± 0.07EIArnett, Sanda, et al., 1967RDSH
8.31PEBaidin, Misharev, et al., 1985Vertical value; LBLHLM
8.28PEHowell, Goncalves, et al., 1984Vertical value; LBLHLM
8.40PEKaim, Tesmann, et al., 1980Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C13H19+9.5 ± 0.1CH3EIOrlov, Misharev, et al., 1986LBLHLM
C13H19+11.69 ± 0.07CH3EIArnett, Sanda, et al., 1967RDSH

References

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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

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