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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -5.42 ± 0.34 | kcal/mol | Ccb | Prosen, Johnson, et al., 1946 |
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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -16.92 ± 0.30 | kcal/mol | Ccb | Prosen, Johnson, et al., 1946 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1401.82 ± 0.27 | kcal/mol | Ccb | Prosen, Johnson, et al., 1946 | Corresponding ΔfHºliquid = -16.90 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1399.80 | kcal/mol | Ccb | Richards and Davis, 1920 | At 291 K; Corresponding ΔfHºliquid = -18.92 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1400.5 | kcal/mol | Ccb | Richards and Barry, 1915 | At 291 K; Corresponding ΔfHºliquid = -18.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 66.61 | cal/mol*K | N/A | Huffman, Parks, et al., 1930 | Extrapolation below 90 K, 67.70 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
56.910 | 294.3 | Huffman, Parks, et al., 1930 | T = 92 to 294 K. Value is unsmoothed experimental datum.; DH |
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
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, 2 | 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 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.336 | 215.0 | Huffman, Parks, et al., 1930 | DH |
Henry's Law 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
---|---|---|---|
0.084 | L | N/A | |
0.085 | V | N/A |
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:
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 |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | Japan AIST/NIMC Database- Spectrum MS-NW- 747 |
NIST MS number | 228190 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D.,
Heats of combustion and formation at 25°C of the alkylbenzenes through C10H14, and of the higher normal monoalkylbenzenes,
J. Res. NBS, 1946, 36, 455-461. [all data]
Richards and Davis, 1920
Richards, T.W.; Davis, H.S.,
The heats of combustion of benzene, toluene, aliphatic alcohols, cyclohexanol, and other carbon compounds,
J. Am. Chem. Soc., 1920, 42, 1599-1617. [all data]
Richards and Barry, 1915
Richards, T.W.; Barry, F.,
The heats of combustion of aromatic hydrocarbons and hexamethylene,
J. Am. Chem. Soc., 1915, 37, 993-1020. [all data]
Huffman, Parks, et al., 1930
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]
Huffman, Parks, et al., 1930, 2
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]
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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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