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

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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
Deltafliquid-45.15 ± 0.35kcal/molEqkNesterova, Verevkin, et al., 1984GLC

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
rhoc1.37mol/lN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 0.079 mol/l; TRC
Quantity Value Units Method Reference Comment
Deltavap15.1 ± 0.02kcal/molEB,IPChirico and Steele, 2009Based on data from 319. - 559. K.; AC
Deltavap14.7 ± 0.07kcal/molGSVerevkin, Kozlova, et al., 2008Based on data from 354. - 382. K.; AC
Deltavap15.1 ± 0.1kcal/molEBSteele, Chirico, et al., 1997, 2Based on data from 387. - 559. K.; AC
Quantity Value Units Method Reference Comment
Deltasub19.8 ± 0.1kcal/molN/AVerevkin, 1998AC

Enthalpy of vaporization

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

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
19.6 ± 0.1310.TVerevkin, 1998Based on data from 288. - 333. K.; AC
19.8305.MEHopke and Sears, 1951Based on data from 285. - 325. K. See also Stephenson and Malanowski, 1987.; AC

Enthalpy of fusion

DeltafusH (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
Deltar0.24 ± 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
Deltar0.354 ± 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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.


Mass spectrum (electron ionization)

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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

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1990.
NIST MS number 114167

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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1.) Enter the desired X axis range (e.g., 100, 200)
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Additional Data

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Source Lang (editor), 1967
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 19127
Instrument Spekromom 201
Melting point 78

Gas Chromatography

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySqualane100.1281.Engewald and Wennrich, 1976N2; Column length: 100. m; Column diameter: 0.23 mm
PackedSE-30150.1298.Shlyakhov, Anvaer, et al., 1975 
PackedSE-30200.1314.Shlyakhov, Anvaer, et al., 1975 
PackedApiezon L150.1319.Shlyakhov, Anvaer, et al., 1975 

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryCarbowax 20M100.1495.1Engewald and Wennrich, 1976N2; Column length: 100. m; Column diameter: 0.23 mm

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillarySPB-51264.Poligné, Collignan, et al., 200160. m/0.32 mm/1. «mu»m, He, 3. K/min; Tstart: 40. C; Tend: 200. C

Normal alkane RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryPEG-40M100.1515.Nesterov, Nesterova, et al., 2000Column length: 50. m
CapillaryPEG-40M100.1516.Nesterov, Nesterova, et al., 2000Column length: 50. m
CapillaryPEG-40M120.1528.Nesterov, Nesterova, et al., 2000Column length: 50. m
CapillaryPEG-40M140.1540.Nesterov, Nesterova, et al., 2000Column length: 50. m
CapillaryPEG-40M160.1552.Nesterov, Nesterova, et al., 2000Column length: 50. m
CapillaryPEG-40M80.1504.Nesterov, Nesterova, et al., 2000Column length: 50. m
CapillaryCarbowax 20M90.1488.Sutter, Peterson, et al., 1997 

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M1488.Ivanciuc, Ivanciuc, et al., 2001Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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]

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]

Orlov, Misharev, et al., 1986
Orlov, V.; Misharev, A.; Takhistox, V., Determination of the enthalpy of formation of para-substituted «alpha»,«alpha»-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 «pi»-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]

Lang (editor), 1967
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1967, 8, 63. [all data]

Engewald and Wennrich, 1976
Engewald, W.; Wennrich, L., Molekülstruktur und Retentionsverhalten. VIII. Zum Retentionsverhalten höherer Alkylbenzole bei der Gas-Verteilungs-Chromatographie, Chromatographia, 1976, 9, 11, 540-547, https://doi.org/10.1007/BF02275960 . [all data]

Shlyakhov, Anvaer, et al., 1975
Shlyakhov, A.F.; Anvaer, B.I.; Zolotareva, O.V.; Romina, N.N.; Novikova, N.V.; Koreshkova, R.I., On the possibility of group indentification of hydrocarbons by gas chromatography from temperature coefficients of retention indices, Zh. Anal. Khim., 1975, 30, 788-792. [all data]

Poligné, Collignan, et al., 2001
Poligné, I.; Collignan, A.; Trystram, G., Characterization of traditional processing of pork meat into boucané, Meat Sci., 2001, 59, 4, 377-389, https://doi.org/10.1016/S0309-1740(01)00090-0 . [all data]

Nesterov, Nesterova, et al., 2000
Nesterov, I.A.; Nesterova, T.N.; Pimerzin, A.A.; Tsvetkov, V.S., Thermodynamics of alkylbenzene sorption and evaporation. IV. Enthalpies of evaporation and thermodynamics chracteristics of sorption by stationary phases OV-101 and PEG-40M, Izvestia vysshikh uchebnykh zavedenii. Khimia i khimicheskaia tekhnologia (Chemistry and chemical technology), 2000, 43, 4, 39-45. [all data]

Sutter, Peterson, et al., 1997
Sutter, J.M.; Peterson, T.A.; Jurs, P.C., Prediction of gas chromatographic retention indices of alkylbenzenes, Anal. Chim. Acta., 1997, 342, 2-3, 113-122, https://doi.org/10.1016/S0003-2670(96)00578-8 . [all data]

Ivanciuc, Ivanciuc, et al., 2001
Ivanciuc, O.; Ivanciuc, T.; Klein, D.J.; Seitz, W.A.; Balaban, A.T., Quantitative structure-retention relationships for gas chromatographic retention indices of alkylbenzenes with molecular graph descriptors, SAR QSAR Environ. Res., 2001, 11, 5-6, 419-452, https://doi.org/10.1080/10629360108035362 . [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References