Benzene, (1-methylethyl)-

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Condensed phase thermochemistry data

Go To: Top, Phase change 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 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
Δfliquid-41.2 ± 1.1kJ/molCcbProsen, Gilmont, et al., 1945Hf by Prosen, Johnson, et al., 1946; ALS
Quantity Value Units Method Reference Comment
Δcliquid-5215.44 ± 0.96kJ/molCcbProsen, Gilmont, et al., 1945Hf by Prosen, Johnson, et al., 1946; Corresponding Δfliquid = -41.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-5218.6kJ/molCcbRichards and Barry, 1915At 291 K; Corresponding Δfliquid = -38.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid277.57J/mol*KN/AKishimoto, Suga, et al., 1973DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
214.4295.96Andolenko and Grigor'ev, 1979T = 296 to 413 K. Unsmoothed experimental datum given as 1.784 kJ/kg*K.; DH
215.40298.15Kishimoto, Suga, et al., 1973T = 14 to 314 K. Glass, 14 to 126 K.; DH
209.41299.8Schlinger and Sage, 1952T = 300 to 366 K.; DH
213.0298.Kurbatov, 1947T = 16 to 153°C, mean Cp, four temperatures.; DH
198.7302.0de Kolossowsky and Udowenko, 1934DH
198.7302.0Kolosovskii and Udovenko, 1934DH

Phase change data

Go To: Top, Condensed phase thermochemistry 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity Value Units Method Reference Comment
Tboil425. ± 1.KAVGN/AAverage of 58 out of 64 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus177.0 ± 0.7KAVGN/AAverage of 13 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple177.13KN/AKishimoto, Suga, et al., 1973, 2Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Tc631.0 ± 0.5KN/ATsonopoulos and Ambrose, 1995 
Tc631.1KN/AAmbrose and Grant, 1957Uncertainty assigned by TRC = 0.15 K; TRC
Tc624.55KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2. K; TRC
Tc635.9KN/AAltschul, 1893Uncertainty assigned by TRC = 4. K; TRC
Quantity Value Units Method Reference Comment
Pc32.1 ± 0.4barN/ATsonopoulos and Ambrose, 1995 
Pc32.09barN/AAmbrose, Broderick, et al., 1967Uncertainty assigned by TRC = 0.06 bar; TRC
Pc27.8644barN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 1.5199 bar; TRC
Pc31.60barN/AAltschul, 1893Uncertainty assigned by TRC = 0.0588 bar; TRC
Quantity Value Units Method Reference Comment
ρc2.32mol/lN/AHales and Townsend, 1972Uncertainty assigned by TRC = 0.008 mol/l; from fit of obs data to 490 K to Rideal's equation; TRC
Quantity Value Units Method Reference Comment
Δvap44. ± 5.kJ/molAVGN/AAverage of 9 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
41.2364.N/ACepeda, Gonzalez, et al., 1989Based on data from 349. to 426. K.; AC
42.1354.AStephenson and Malanowski, 1987Based on data from 339. to 433. K.; AC
41.9358.MMForziati, Norris, et al., 1949Based on data from 343. to 426. K. See also Willingham, Taylor, et al., 1945.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference
343.17 to 426.524.054191455.811-65.948Williamham, Taylor, et al., 1945

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
7.326177.13Kishimoto, Suga, et al., 1973DH
7.32177.1Kishimoto, Suga, et al., 1973AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
41.36177.13Kishimoto, Suga, et al., 1973DH
41.37177.1Kishimoto, Suga, et al., 1973, 2CAL

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:


Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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

View reactions leading to C9H12+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.73 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)791.6kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity763.9kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.72EIMcLoughlin, Morrison, et al., 1979LLK
8.725 ± 0.008EQLias and Ausloos, 1978LLK
8.69 ± 0.01PIWatanabe, 1957RDSH
~8.76SHammond, Price, et al., 1950RDSH
8.71PEHowell, Goncalves, et al., 1984Vertical value; LBLHLM
8.75PEShudo, Kobayashi, et al., 1977Vertical value; LLK
8.98PEBruckmann and Klessinger, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H7+9.91C2H5EIMcLoughlin, Morrison, et al., 1979LLK
C8H9+10.02CH3EIMcLoughlin, Morrison, et al., 1979LLK
C8H9+10.65CH3EIHowe and Williams, 1969RDSH

De-protonation reactions

C9H11- + Hydrogen cation = Benzene, (1-methylethyl)-

By formula: C9H11- + H+ = C9H12

Quantity Value Units Method Reference Comment
Δr1585. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1560. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, 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: 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 114201

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References

Go To: Top, Condensed phase thermochemistry data, Phase change 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, Gilmont, et al., 1945
Prosen, E.J.; Gilmont, R.; Rossini, F.D., Heats of combustion of benzene, toluene, ethyl-benzene, o-xylene, m-xylene, p-xylene, n-propylbenzene, and styrene, J. Res. NBS, 1945, 34, 65-70. [all data]

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 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]

Kishimoto, Suga, et al., 1973
Kishimoto, K.; Suga, H.; Syuzo, S., Calorimetric study of the glassy state. VIII. Heat capacity and relaxational phenomena of isopropylbenzene, Bull. Chem. Soc. Japan, 1973, 46, 3020-3031. [all data]

Andolenko and Grigor'ev, 1979
Andolenko, R.A.; Grigor'ev, B.A., Investigation of isobaric heat capacity of aromatic hydrocarbons at atmospheric pressure, Iaz. Vyssh. Ucheb. Zaved., Neft i Gaz (11), 1979, 78, 90. [all data]

Schlinger and Sage, 1952
Schlinger, W.G.; Sage, B.H., Isobaric heat capacities at bubble point. cis-2-butene, isopropylbenzene, and n-decane, Ind. Eng. Chem., 1952, 44, 2454-2456. [all data]

Kurbatov, 1947
Kurbatov, V.Ya., Specific heat of liquids. I. Specific heat of benzenoid hydrocarbons, Zhur. Obshch. Khim., 1947, 17, 1999-2003. [all data]

de Kolossowsky and Udowenko, 1934
de Kolossowsky, N.; Udowenko, W.W., Determination des chaleurs specifiques des liquides, Compt. rend., 1934, 198, 1394-1395. [all data]

Kolosovskii and Udovenko, 1934
Kolosovskii, N.A.; Udovenko, W.W., Specific heat of liquids. II., Zhur. Obshchei Khim., 1934, 4, 1027-1033. [all data]

Kishimoto, Suga, et al., 1973, 2
Kishimoto, K.; Suga, H.; Seki, S., Calorimetric Study of the Glassy State. VIII. Heat Capacity and Relaxational Phenomena of Isopropylbenzene, Bull. Chem. Soc. Japan, 1973, 46, 10, 3020, https://doi.org/10.1246/bcsj.46.3020 . [all data]

Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons, J. Chem. Eng. Data, 1995, 40, 547-558. [all data]

Ambrose and Grant, 1957
Ambrose, D.; Grant, D.G., The Critical Temperatures of Some Hydrocarbons and Pyridine Bases, Trans. Faraday Soc., 1957, 53, 771. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Altschul, 1893
Altschul, M., The critical values of some organic compounds, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1893, 11, 577. [all data]

Ambrose, Broderick, et al., 1967
Ambrose, D.; Broderick, B.E.; Townsend, R., The Vapour Pressures above the Normal Boiling Point and the Critical Pressures of Some Aromatic Hydrocarbons, J. Chem. Soc. , 1967, 1967, 1967, 633-41. [all data]

Hales and Townsend, 1972
Hales, J.L.; Townsend, R., Liquid Densities from 293 to 490 K of Nine Aromatic Hydrocarbons, J. Chem. Thermodyn., 1972, 4, 763-72. [all data]

Cepeda, Gonzalez, et al., 1989
Cepeda, Emilio; Gonzalez, Cristina; Resa, Jose M., Isobaric vapor-liquid equilibrium for the cumene-phenol system, J. Chem. Eng. Data, 1989, 34, 3, 270-273, https://doi.org/10.1021/je00057a004 . [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]

Willingham, Taylor, et al., 1945
Willingham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor pressures and boiling points of some paraffin, alkylcyclopentane, alkylcyclohexane, and alkylbenzene hydrocarbons, J. RES. NATL. BUR. STAN., 1945, 35, 3, 219-17, https://doi.org/10.6028/jres.035.009 . [all data]

Williamham, Taylor, et al., 1945
Williamham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor Pressures and Boiling Points of Some Paraffin, Alkylcyclopentane, Alkylcyclohexane, and Alkylbenzene Hydrocarbons, J. Res. Natl. Bur. Stand. (U.S.), 1945, 35, 3, 219-244, https://doi.org/10.6028/jres.035.009 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [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]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Hammond, Price, et al., 1950
Hammond, V.J.; Price, W.C.; Teegan, J.P.; Walsh, A.D., The absorption spectra of some substituted benzenes and naphthalenes in the vacuum ultra-violet, Faraday Discuss. Chem. Soc., 1950, 9, 53. [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]

Shudo, Kobayashi, et al., 1977
Shudo, K.; Kobayashi, T.; Utsunomiya, C., Photoelectron spectral studies on the interaction of three-membered rings with aryl groups, Tetrahedron, 1977, 33, 1721. [all data]

Bruckmann and Klessinger, 1974
Bruckmann, P.; Klessinger, M., Photoelektronenspektren organischer verbindungen. V. Wechselwirkung kleiner ringe mit π-systemen, Chem. Ber., 1974, 107, 1108. [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]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References