Ethylbenzene
- Formula: C8H10
- Molecular weight: 106.1650
- IUPAC Standard InChIKey: YNQLUTRBYVCPMQ-UHFFFAOYSA-N
- CAS Registry Number: 100-41-4
- 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. - Isotopologues:
- Other names: Benzene, ethyl-; Ethylbenzol; EB; Phenylethane; Aethylbenzol; Ethylbenzeen; Etilbenzene; Etylobenzen; NCI-C56393; UN 1175; α-Methyltoluene; NSC 406903
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Reaction thermochemistry data
Go To: Top, 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:
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- + =
By formula: C8H9- + H+ = C8H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 406.0 ± 4.6 | kcal/mol | CIDT | Graul and Squires, 1990 | gas phase; From decarboxylation threshold. Stable form probably the spiro[2.5]octadienide Maas and van Keelen, 1989; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 397.7 ± 4.7 | kcal/mol | H-TS | Graul and Squires, 1990 | gas phase; From decarboxylation threshold. Stable form probably the spiro[2.5]octadienide Maas and van Keelen, 1989; B |
C8H9- + =
By formula: C8H9- + H+ = C8H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 379.7 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 373.3 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: 2H2 + C8H6 = C8H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -66.12 ± 0.06 | kcal/mol | Chyd | Davis, Allinger, et al., 1985 | liquid phase; solvent: Hexane; ALS |
ΔrH° | -64.7 ± 0.9 | kcal/mol | Chyd | Rogers and McLafferty, 1971 | liquid phase; solvent: Hydrocarbon; ALS |
ΔrH° | -70.7 ± 1.0 | kcal/mol | Chyd | Flitcroft and Skinner, 1958 | liquid phase; ALS |
By formula: NO- + C8H10 = (NO- • C8H10)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 44.5 | kcal/mol | ICR | Reents and Freiser, 1981 | gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M |
By formula: C8H10 + 3H2 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -48.18 ± 0.10 | kcal/mol | Chyd | Dolliver, Gresham, et al., 1937 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -48.9 ± 0.1 kcal/mol; At 355 °K; ALS |
By formula: Cl- + C8H10 = (Cl- • C8H10)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 5.00 | kcal/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
5.0 | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
+ = C8H9Br +
By formula: C8H10 + C6H5Br = C8H9Br + C6H6
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0.14 ± 0.0050 | kcal/mol | Cm | Merdzhanov, Alenin, et al., 1982 | gas phase; Heat of isomerization at 349 K; ALS |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28.01 ± 0.41 | kcal/mol | Chyd | Abboud, Jimenez, et al., 1995 | liquid phase; solvent: Hydrocarbon; Like gas phase; ALS |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 29.840 | kcal/mol | Eqk | Ghosh, Ram Das Guha, et al., 1945 | gas phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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