Ethylbenzene

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid-2.98 ± 0.20kcal/molCcbProsen, Gilmont, et al., 1945Hf by Prosen, Johnson, et al., 1946; ALS
Δfliquid1.6 ± 0.96kcal/molCcbN/Arecalculated with modern CO2,H2O thermo; estimated uncertainty (NOTE all values in source also have wrong sign); DRB
Δfliquid6.5kcal/molCcbMoureu and Andre, 1914ALS
Quantity Value Units Method Reference Comment
Δcliquid-1092. ± 4.kcal/molAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
liquid60.949cal/mol*KN/AGuthrie, Spitzer, et al., 1944DH
liquid61.21cal/mol*KN/AHuffman, Parks, et al., 1930Extrapolation below 90 K, 61.09 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
44.17293.31Andolenko and Grigor'ev, 1979T = 293 to 393 K. Unsmoothed experimental datum given as 1.741 kJ/kg*K.; DH
44.3528298.15Fortier and Benson, 1979DH
44.3497298.15Fortier and Benson, 1977DH
44.402298.15Fortier, Benson, et al., 1976DH
38.5295.Tschamler, 1948DH
44.41298.Kurbatov, 1947T = 15 to 18 C, mean Cp, four temperatures.; DH
44.465298.15Scott and Brickwedde, 1945T = 15 to 300 K.; DH
44.410298.15Guthrie, Spitzer, et al., 1944T = 13 to 305 K.; DH
42.71302.8de Kolossowsky and Udowenko, 1934DH
42.71302.7Kolosovskii and Udovenko, 1934DH
44.60298.15Blacet, Leighton, et al., 1931T = 286 to 368 K. Heat capacity reported as 0.420 cal g-1 K-1 at 25 C.; DH
43.91298.5Smith and Andrews, 1931T = 102 to 299 K. Value is unsmoothed experimental datum.; DH
43.40297.4Huffman, Parks, et al., 1930T = 93 to 305 K. Value is unsmoothed experimental datum.; DH
43.40303.Willams and Daniels, 1924T = 303 to 343 K. Equation only.; DH
44.10298.von Reis, 1881T = 292 to 425 K.; DH

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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C8H9- + Hydrogen cation = Ethylbenzene

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Δr406.0 ± 4.6kcal/molCIDTGraul and Squires, 1990gas phase; From decarboxylation threshold. Stable form probably the spiro[2.5]octadienide Maas and van Keelen, 1989; B
Quantity Value Units Method Reference Comment
Δr397.7 ± 4.7kcal/molH-TSGraul and Squires, 1990gas phase; From decarboxylation threshold. Stable form probably the spiro[2.5]octadienide Maas and van Keelen, 1989; B

C8H9- + Hydrogen cation = Ethylbenzene

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Δr379.7 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr373.3 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

2Hydrogen + Phenylethyne = Ethylbenzene

By formula: 2H2 + C8H6 = C8H10

Quantity Value Units Method Reference Comment
Δr-66.12 ± 0.06kcal/molChydDavis, Allinger, et al., 1985liquid phase; solvent: Hexane; ALS
Δr-64.7 ± 0.9kcal/molChydRogers and McLafferty, 1971liquid phase; solvent: Hydrocarbon; ALS
Δr-70.7 ± 1.0kcal/molChydFlitcroft and Skinner, 1958liquid phase; ALS

Nitric oxide anion + Ethylbenzene = (Nitric oxide anion • Ethylbenzene)

By formula: NO- + C8H10 = (NO- • C8H10)

Quantity Value Units Method Reference Comment
Δr44.5kcal/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Ethylbenzene + 3Hydrogen = Cyclohexane, ethyl-

By formula: C8H10 + 3H2 = C8H16

Quantity Value Units Method Reference Comment
Δr-48.18 ± 0.10kcal/molChydDolliver, Gresham, et al., 1937gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -48.9 ± 0.1 kcal/mol; At 355 °K; ALS

Chlorine anion + Ethylbenzene = (Chlorine anion • Ethylbenzene)

By formula: Cl- + C8H10 = (Cl- • C8H10)

Quantity Value Units Method Reference Comment
Δr5.00kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
5.0300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

Ethylbenzene + Benzene, bromo- = C8H9Br + Benzene

By formula: C8H10 + C6H5Br = C8H9Br + C6H6

Quantity Value Units Method Reference Comment
Δr-0.14 ± 0.0050kcal/molCmMerdzhanov, Alenin, et al., 1982gas phase; Heat of isomerization at 349 K; ALS

Styrene + Hydrogen = Ethylbenzene

By formula: C8H8 + H2 = C8H10

Quantity Value Units Method Reference Comment
Δr-28.01 ± 0.41kcal/molChydAbboud, Jimenez, et al., 1995liquid phase; solvent: Hydrocarbon; Like gas phase; ALS

Ethylbenzene = Styrene + Hydrogen

By formula: C8H10 = C8H8 + H2

Quantity Value Units Method Reference Comment
Δr29.840kcal/molEqkGhosh, Ram Das Guha, et al., 1945gas phase; ALS

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
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 C8H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.77 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)188.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity181.7kcal/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
188.8Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
181.7Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.77PEHowell, Goncalves, et al., 1984LBLHLM
8.61PEKlasinc, Kovac, et al., 1983LBLHLM
8.65 ± 0.10EISelim and Helal, 1982LBLHLM
8.76EIMcLoughlin, Morrison, et al., 1979LLK
8.768 ± 0.008EQLias and Ausloos, 1978LLK
8.75 ± 0.05PIAkopyan and Vilesov, 1966RDSH
8.76 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
8.77 ± 0.01SHammond, Price, et al., 1950RDSH
8.77PEHowell, Goncalves, et al., 1984Vertical value; LBLHLM
8.73PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
9.38PEDeshmukh, Dutta, et al., 1982Vertical value; LBLHLM

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H5+16.2 ± 0.2C2H2+CH3EITajima and Tsuchiya, 1973LLK
C6H6+11.0 ± 0.1C2H4?PIAkopyan and Vilesov, 1966RDSH
C7H7+9.9 ± 0.1CH3TRPILifshitz and Malinovich, 1984LBLHLM
C7H7+10.15 ± 0.10CH3EISelim and Helal, 1982LBLHLM
C7H7+10.06CH3EIMcLoughlin, Morrison, et al., 1979LLK
C7H7+10.9 ± 0.1CH3PIAkopyan and Vilesov, 1966RDSH
C8H9+10.60HEIMcLoughlin, Morrison, et al., 1979LLK
C8H9+12.1 ± 0.1HPIAkopyan and Vilesov, 1966RDSH
C8H9+11.4 ± 0.1HEIMeyer, Haynes, et al., 1965RDSH

De-protonation reactions

C8H9- + Hydrogen cation = Ethylbenzene

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Δr406.0 ± 4.6kcal/molCIDTGraul and Squires, 1990gas phase; From decarboxylation threshold. Stable form probably the spiro[2.5]octadienide Maas and van Keelen, 1989; B
Quantity Value Units Method Reference Comment
Δr397.7 ± 4.7kcal/molH-TSGraul and Squires, 1990gas phase; From decarboxylation threshold. Stable form probably the spiro[2.5]octadienide Maas and van Keelen, 1989; B

C8H9- + Hydrogen cation = Ethylbenzene

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Δr379.7 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr373.3 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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.

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]

Moureu and Andre, 1914
Moureu, C.; Andre, E., Thermochimie des composes acetyleniques, Ann. Chim. Phys., 1914, 1, 113-145. [all data]

Guthrie, Spitzer, et al., 1944
Guthrie, G.B., Jr.; Spitzer, R.W.; Huffman, H.M., Thermal data. XVIII. The heat capacity, heat of fusion, entropy and free energy of ethylbenzene, J. Am. Chem. Soc., 1944, 66, 2120-2121. [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]

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]

Fortier and Benson, 1979
Fortier, J.-L.; Benson, G.C., Heat capacities of some binary aromatic hydrocarbon mixtures containing benzene or toluene, J. Chem. Eng. Data, 1979, 24(1), 34-37. [all data]

Fortier and Benson, 1977
Fortier, J.-L.; Benson, G.C., Excess heat capacities of binary mixtures of tetrachloromethane witlh some aromatic liquids at 298.15 K, J. Chem. Thermodynam., 1977, 9, 1181-1188. [all data]

Fortier, Benson, et al., 1976
Fortier, J.-L.; Benson, G.C.; Picker, P., Heat capacities of some organic liquids determined with the Picker flow calorimeter, J. Chem. Thermodynam., 1976, 8, 289-299. [all data]

Tschamler, 1948
Tschamler, H., Uber binare flussige Mischungen I. Mischungswarment, Volumseffekte und Zustandsdiagramme von chlorex mit benzol und n-alkylbenzolen, Monatsh. Chem., 1948, 79, 162-177. [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]

Scott and Brickwedde, 1945
Scott, R.B.; Brickwedde, F.G., Thermodynamic properties of solid and liquid ethylbenzene from 0 to 300K, J. Res., 1945, NBS 35, 501-512. [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]

Blacet, Leighton, et al., 1931
Blacet, F.E.; Leighton, P.A.; Bartlett, E.P., The specific heats of five pure organic liquids and of ethyl alcohol-water mixtures, J. Phys. Chem., 1931, 35, 1935-1943. [all data]

Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H., Thermal energy studies. I. Phenyl derivatives of methane, ethane and some related compounds. J. Am. Chem. Soc., 1931, 53, 3644-3660. [all data]

Willams and Daniels, 1924
Willams, J.W.; Daniels, F., The specific heats of certain organic liquids at elevated temperatures, J. Am. Chem. Soc., 1924, 46, 903-917. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Maas and van Keelen, 1989
Maas, W.P.M.; van Keelen, P.A., On the Generation and Characterization of the Spiro[2,5]Octadienyl Anion in the Gas Phase, Org. Mass Spectrom., 1989, 24, 8, 546, https://doi.org/10.1002/oms.1210240807 . [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]

Davis, Allinger, et al., 1985
Davis, H.E.; Allinger, N.L.; Rogers, D.W., Enthalpies of hydrogenation of phenylalkynes: indirect determination of the enthalpy of formation of diphenylcyclopropenone, J. Org. Chem., 1985, 50, 3601-3604. [all data]

Rogers and McLafferty, 1971
Rogers, D.W.; McLafferty, F.J., A new hydrogen calorimeter. Heats of hydrogenation of allyl and vinyl unsaturation adjacent to a ring, Tetrahedron, 1971, 27, 3765-3775. [all data]

Flitcroft and Skinner, 1958
Flitcroft, T.L.; Skinner, H.A., Heats of hydrogenation Part 2.-Acetylene derivatives, Trans. Faraday Soc., 1958, 54, 47-53. [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E., Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons, J. Am. Chem. Soc., 1937, 59, 831-841. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-, Can. J. Chem., 1982, 60, 1907. [all data]

Merdzhanov, Alenin, et al., 1982
Merdzhanov, V.R.; Alenin, V.I.; Nesterova, T.N.; Rozhnov, A.M., Study of equilibrium transformation of ethylbromobenzenes, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1982, 25, 1047-1049. [all data]

Abboud, Jimenez, et al., 1995
Abboud, J.-L.M.; Jimenez, P.; Roux, M.V.; Turrion, C.; Lopez-Mardomingo, C.; Podosenin, A.; Rogers, D.W.; Liebman, J.F., Interrelations of the energetics of amides and alkenes: enthalpies of formation of N,N-dimethyl dertivatives of pivalamide, 1-adamantylcarboxamide and benzamide, and of styrene and its a-, trans-β- and β,β-methylated derivates, J. Phys. Org. Chem., 1995, 8, 15-25. [all data]

Ghosh, Ram Das Guha, et al., 1945
Ghosh, J.C.; Ram Das Guha, S.; Roy, A.N., Chemical equilibrium in styrene formation from ethyl-benzene at low pressures, Curr. Sci., 1945, 14, 269. [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]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [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]

Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H., Photoelectron spectra of acenes. Electronic structure and substituent effects, Pure Appl. Chem., 1983, 55, 289. [all data]

Selim and Helal, 1982
Selim, E.T.M.; Helal, A.I., The study of C1-C3 monosubstituted alkyl benzenes by the inverse convolution of first differential ionization efficiency curves, Org. Mass Spectrom., 1982, 17, 539. [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]

Akopyan and Vilesov, 1966
Akopyan, M.E.; Vilesov, F.I., A mass-spectrometric study of the photo-ionisation of benzene derivatives at wavelengths up to 885 A, Zh. Fiz. Khim., 1966, 40, 125, In original 63. [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]

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]

Deshmukh, Dutta, et al., 1982
Deshmukh, P.; Dutta, T.K.; Hwang, J.L.-S.; Housecroft, C.E.; Fehlner, T.P., Photoelectron spectroscopic measurements of the relative charge on carbyne fragments bound to polynuclear cobalt carbonyl clusters, J. Am. Chem. Soc., 1982, 104, 1740. [all data]

Tajima and Tsuchiya, 1973
Tajima, S.; Tsuchiya, T., Energetics consideration of C5H5+ ions produced from various precursors by electron impact, Bull. Chem. Soc. Jpn., 1973, 46, 3291. [all data]

Lifshitz and Malinovich, 1984
Lifshitz, C.; Malinovich, Y., Time resolved photoionization mass spectrometry in the millisecond range, Int. J. Mass Spectrom. Ion Processes, 1984, 60, 99. [all data]

Meyer, Haynes, et al., 1965
Meyer, F.; Haynes, P.; McLean, S.; Harrison, A.G., An electron impact study of some C8H10 isomers, Can. J. Chem., 1965, 43, 211. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References