Styrene

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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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

styrenide anion + Hydrogen cation = Styrene

By formula: C8H7- + H+ = C8H8

Quantity Value Units Method Reference Comment
Δr391.0 ± 2.5kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; Acid: styrene. AM1 says ortho deprotonation prefered to alpha. Anchored to 88MEO scale.; B
Quantity Value Units Method Reference Comment
Δr383.4 ± 2.0kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; Acid: styrene. AM1 says ortho deprotonation prefered to alpha. Anchored to 88MEO scale.; B

C3H9Si+ + Styrene = (C3H9Si+ • Styrene)

By formula: C3H9Si+ + C8H8 = (C3H9Si+ • C8H8)

Quantity Value Units Method Reference Comment
Δr36.6kcal/molPHPMSLi and Stone, 1989gas phase; condensation; M
Quantity Value Units Method Reference Comment
Δr42.4cal/mol*KPHPMSLi and Stone, 1989gas phase; condensation; M

Styrene + 4Hydrogen = Cyclohexane, ethyl-

By formula: C8H8 + 4H2 = C8H16

Quantity Value Units Method Reference Comment
Δr-76.50 ± 0.25kcal/molChydDolliver, Gresham, et al., 1937gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -77.48 ± 0.20 kcal/mol; At 355 °K; ALS

(CAS Reg. No. 13822-53-2 • 4294967295Styrene) + Styrene = CAS Reg. No. 13822-53-2

By formula: (CAS Reg. No. 13822-53-2 • 4294967295C8H8) + C8H8 = CAS Reg. No. 13822-53-2

Quantity Value Units Method Reference Comment
Δr48.9 ± 2.2kcal/molN/ABartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

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

Styrene + Hydrogen chloride = Benzene, (1-chloroethyl)-

By formula: C8H8 + HCl = C8H9Cl

Quantity Value Units Method Reference Comment
Δr-13.3 ± 1.7kcal/molCmNesterova, Kovzel, et al., 1977liquid phase; Hydrochlorination; ALS

Hydrogen bromide + Styrene = Benzene, (1-bromoethyl)-

By formula: HBr + C8H8 = C8H9Br

Quantity Value Units Method Reference Comment
Δr-16.5 ± 1.7kcal/molCmNesterova, Kovzel, et al., 1977liquid phase; Hydrobromination; ALS

1,3,5,7-Cyclooctatetraene = Styrene

By formula: C8H8 = C8H8

Quantity Value Units Method Reference Comment
Δr-34.35 ± 0.34kcal/molCisoProsen, Johnson, et al., 1947liquid 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

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Li and Stone, 1989
Li, X.; Stone, J.A., Determination of the beta silicon effect from a mass spectrometric study of the association of trimethylsilylium ion with alkenes, J. Am. Chem. Soc., 1989, 111, 15, 5586, https://doi.org/10.1021/ja00197a013 . [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]

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]

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]

Nesterova, Kovzel, et al., 1977
Nesterova, T.N.; Kovzel, E.N.; Karaseva, S.Ya.; Rozhnov, A.M., Heats of reaction of the hydrohalogenation of styrene and α-methylstyrene, Vses. Konf. Kalorim. Rasshir. Tezisy Dokl. 7th, 1977, 1, 132. [all data]

Prosen, Johnson, et al., 1947
Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heat of combustion and formation of 1,3,5,7-cyclooctatetraene and its heat of isomerization to styrene, J. Am. Chem. Soc., 1947, 69, 2068-2069. [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

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