Benzene, tert-butyl-
- Formula: C10H14
- Molecular weight: 134.2182
- IUPAC Standard InChIKey: YTZKOQUCBOVLHL-UHFFFAOYSA-N
- CAS Registry Number: 98-06-6
- 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, (1,1-dimethylethyl)-; tert-Butylbenzene; Dimethylethylbenzene; Phenyltrimethylmethane; Pseudobutylbenzene; Trimethylphenylmethane; 2-Methyl-2-Phenylpropane; 1,1-Dimethylethyl-benzene; t-Butylbenzene; 2-Phenyl-2-methylpropane; Benzene, t-butyl-; NSC 6557; α-dimethylethylbenzene
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Phase change data
Go To: Top, 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:
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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 442. ± 2. | K | AVG | N/A | Average of 47 out of 48 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 215. ± 2. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 215.0 | K | N/A | Huffman, Parks, et al., 1930 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.5 ± 0.3 | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.8 ± 0.05 | 340. | EB | Steele, Chirico, et al., 2002 | Based on data from 332. to 486. K.; AC |
10.2 ± 0.05 | 380. | EB | Steele, Chirico, et al., 2002 | Based on data from 332. to 486. K.; AC |
9.54 ± 0.07 | 420. | EB | Steele, Chirico, et al., 2002 | Based on data from 332. to 486. K.; AC |
8.8 ± 0.1 | 460. | EB | Steele, Chirico, et al., 2002 | Based on data from 332. to 486. K.; AC |
11.4 ± 0.1 | 293. | GS | Verevkin, 1998 | Based on data from 278. to 308. K.; AC |
10.3 | 383. | A | Stephenson and Malanowski, 1987 | Based on data from 368. to 444. K.; AC |
10.4 | 372. | N/A | Forziati, Norris, et al., 1949 | Based on data from 357. to 443. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
357.03 to 443.31 | 4.0397 | 1504.572 | -69.822 | Forziati, Norris, et al., 1949, 2 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
2.0 | 215.3 | DSC,AC | Chirico and Steele, 2009 | AC |
2.01 | 215. | N/A | Domalski and Hearing, 1996 | AC |
2.007 | 215.0 | N/A | Huffman, Parks, et al., 1930, 2 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.336 | 215.0 | Huffman, Parks, et al., 1930, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, References, Notes
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:
L - 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.68 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.69 | PI | Domnin, Lakshin, et al., 1985 | LBLHLM |
8.25 | PE | Baidin, Misharev, et al., 1985 | LBLHLM |
8.63 ± 0.01 | PI | VanderGreef, 1980 | LLK |
8.69 | EI | McLoughlin, Morrison, et al., 1979 | LLK |
8.725 ± 0.008 | EQ | Lias and Ausloos, 1978 | LLK |
8.64 | CTS | Pitt, 1973 | LLK |
8.68 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.68 ± 0.01 | PI | Price, Bralsford, et al., 1959 | RDSH |
8.81 | PE | Baidin, Misharev, et al., 1985 | Vertical value; LBLHLM |
8.65 | PE | Howell, Goncalves, et al., 1984 | Vertical value; LBLHLM |
8.74 ± 0.05 | PE | Nagy-Felsobuki and Peel, 1979 | Vertical value; LLK |
8.83 | PE | Bischof, Dewar, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C9H11+ | 9.66 | CH3 | PI | Domnin, Lakshin, et al., 1985 | LBLHLM |
C9H11+ | 9.73 ± 0.02 | CH3 | PIPECO | Brand and Baer, 1983 | T = 298K; LBLHLM |
C9H11+ | 9.93 ± 0.03 | CH3 | PIPECO | Brand and Baer, 1983 | T = 0K; LBLHLM |
C9H11+ | 10.26 | CH3 | EI | Howe and Williams, 1969 | RDSH |
References
Go To: Top, Phase change 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.
Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Thomas, S.B.,
Thermal Data on Organic Compounds. VII The Heat Capacities, Entropies and Free Energies of the Isomeric Heptanes,
J. Am. Chem. Soc., 1930, 52, 3241. [all data]
Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor Pressure, Heat Capacity, and Density along the Saturation Line: Measurements for Benzenamine, Butylbenzene, sec -Butylbenzene, tert -Butylbenzene, 2,2-Dimethylbutanoic Acid, Tridecafluoroheptanoic Acid, 2-Butyl-2-ethyl-1,3-propanediol, 2,2,4-Trimethyl-1,3-pentanediol, and 1-Chloro-2-propanol,
J. Chem. Eng. Data, 2002, 47, 4, 648-666, https://doi.org/10.1021/je010083e
. [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]
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]
Forziati, Norris, et al., 1949
Forziati, Alphonse F.; Norris, William R.; Rossini, Frederick D.,
Vapor pressures and boiling points of sixty API-NBS hydrocarbons,
J. RES. NATL. BUR. STAN., 1949, 43, 6, 555-17, https://doi.org/10.6028/jres.043.050
. [all data]
Forziati, Norris, et al., 1949, 2
Forziati, A.F.; Norris, W.R.; Rossini, F.D.,
Vapor Pressures and Boiling Points of Sixty API-NBS Hydrocarbons,
J. Res. Natl. Bur. Stand. (U.S.), 1949, 43, 6, 555-563, https://doi.org/10.6028/jres.043.050
. [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]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Huffman, Parks, et al., 1930, 2
Huffman, H.M.; Parks, G.S.; Daniels, A.C.,
Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons,
J. Am. Chem. Soc., 1930, 52, 1547-1558. [all data]
Domnin, Lakshin, et al., 1985
Domnin, I.N.; Lakshin, A.M.; Misharev, A.D.; Orlov, V.M.; Takhistov, V.V.,
Thermochemical investigation of some hydrocarbon ions generated by photoionization,
J. Org. Chem. USSR, 1985, 21, 1149. [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]
VanderGreef, 1980
VanderGreef, J.,
[Title unavailable], Thesis, Amsterdam, 1980. [all data]
McLoughlin, Morrison, et al., 1979
McLoughlin, R.G.; Morrison, J.D.; Traeger, J.C.,
Photoionization of the C-1 - C-4 monosubstituted alkyl benzenes: Thermochemistry of [C7H7]+ and [C8H9]+ formation,
Org. Mass Spectrom., 1979, 14, 104. [all data]
Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J.,
eIonization energies of organic compounds by equilibrium measurements,
J. Am. Chem. Soc., 1978, 100, 6027. [all data]
Pitt, 1973
Pitt, C.G.,
Hyperconjugation and its role in group IV chemistry,
J. Organomet. Chem., 1973, 61, 49. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Price, Bralsford, et al., 1959
Price, W.C.; Bralsford, R.; Harris, P.V.; Ridley, R.G.,
Ultra-violet spectra and ionization potentials of hydrocarbon molecules,
Spectrochim. Acta, 1959, 14, 45. [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]
Nagy-Felsobuki and Peel, 1979
Nagy-Felsobuki, E.; Peel, J.B.,
Photoelectron spectroscopic studies of the butylbenzenes,
J. Electron Spectrosc. Relat. Phenom., 1979, 16, 397. [all data]
Bischof, Dewar, et al., 1974
Bischof, P.K.; Dewar, M.J.S.; Goodman, D.W.; Jones, T.B.,
Photoelectron spectra of molecules. VI. Hyperconjugation versus pπ-dπ bonding in group IVb compounds,
J. Organomet. Chem., 1974, 82, 89. [all data]
Brand and Baer, 1983
Brand, W.A.; Baer, T.,
Unimolecular dissociation of energy-selected t-butylbenzene ions and effect of thermal energy on data analysis,
Int. J. Mass Spectrom. Ion Phys., 1983, 49, 103. [all data]
Howe and Williams, 1969
Howe, I.; Williams, D.H.,
Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes,
J. Am. Chem. Soc., 1969, 91, 7137. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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