2-Butene, (E)-

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

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Individual Reactions

2-Butene, (Z)- = 2-Butene, (E)-

By formula: C4H8 = C4H8

Quantity Value Units Method Reference Comment
Δr-0.9 ± 0.5kcal/molAVGN/AAverage of 7 values; Individual data points

1-Butene = 2-Butene, (E)-

By formula: C4H8 = C4H8

Quantity Value Units Method Reference Comment
Δr-3.00 ± 0.20kcal/molEqkMeyer and Stroz, 1972gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -2.64 kcal/mol; At 300 K; ALS
Δr-2.96 ± 0.40kcal/molEqkHappel, Hnatow, et al., 1971gas phase; ALS
Δr-3.03kcal/molEqkMaccoll and Ross, 1965gas phase; GC; ALS
Δr-2.80 ± 0.20kcal/molEqkGolden, Egger, et al., 1964gas phase; ALS
Δr-2.75kcal/molCisoLevanova and Andreevskii, 1964gas phase; At 420.3 K; ALS

Hydrogen bromide + 2-Butene, (E)- = Butane, 2-bromo-

By formula: HBr + C4H8 = C4H9Br

Quantity Value Units Method Reference Comment
Δr-17.26 ± 0.12kcal/molCmLacher, Billings, et al., 1952gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -17.3 ± 1.4 kcal/mol; Heat of hydrobromination at 373 K; ALS

C3H9Si+ + 2-Butene, (E)- = (C3H9Si+ • 2-Butene, (E)-)

By formula: C3H9Si+ + C4H8 = (C3H9Si+ • C4H8)

Quantity Value Units Method Reference Comment
Δr30.9kcal/molPHPMSLi and Stone, 1989gas phase; condensation; M
Quantity Value Units Method Reference Comment
Δr41.5cal/mol*KPHPMSLi and Stone, 1989gas phase; condensation; M

Hydrogen + 2-Butene, (E)- = Butane

By formula: H2 + C4H8 = C4H10

Quantity Value Units Method Reference Comment
Δr-27.38 ± 0.10kcal/molChydKistiakowsky, Ruhoff, et al., 1935gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -27.621 ± 0.021 kcal/mol; At 355 °K; ALS

2-Butene, (E)- + Bromine = erythro-2,3-Dibromobutane

By formula: C4H8 + Br2 = C4H8Br2

Quantity Value Units Method Reference Comment
Δr-28.95 ± 0.20kcal/molCmConn, Kistiakowsky, et al., 1938gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -29.08 ± 0.20 kcal/mol; At 355 °K; ALS

Butane, 2-chloro- = 2-Butene, (E)- + Hydrogen chloride

By formula: C4H9Cl = C4H8 + HCl

Quantity Value Units Method Reference Comment
Δr15.25kcal/molEqkLevanova and Andreevskii, 1964gas phase; At 420 K; ALS

2-Butene, (E)- + Ethylene = cyclobutane, 1,2-dimethyl-, trans-

By formula: C4H8 + C2H4 = C6H12

Quantity Value Units Method Reference Comment
Δr-16.7kcal/molEqkScacchi and Back, 1977liquid 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.

Meyer and Stroz, 1972
Meyer, E.F.; Stroz, D.G., Thermodynamics of n-butene isomerization, J. Am. Chem. Soc., 1972, 94, 6344-6347. [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]

Happel, Hnatow, et al., 1971
Happel, J.; Hnatow, M.A.; Mezaki, R., Isomerization equilibrium constants of n-butenes, J. Chem. Eng. Data, 1971, 16, 206-209. [all data]

Maccoll and Ross, 1965
Maccoll, A.; Ross, R.A., The hydrogen bromide catalyzed isomerization of n-butenes. I. equilibrium values, J. Am. Chem. Soc., 1965, 87, 1169-1170. [all data]

Golden, Egger, et al., 1964
Golden, D.M.; Egger, K.W.; Benson, S.W., Iodine-catalyzed isomerization of olefins. I. Thermodynamics data from equilibrium studies of positional and geometrical isomerization of 1-butene and 2-butene, J. Am. Chem. Soc., 1964, 86, 5416-5420. [all data]

Levanova and Andreevskii, 1964
Levanova, S.V.; Andreevskii, D.N., The equilibrium of 2-chlorobutane dehydrochlorination, Neftekhimiya, 1964, 4, 329-336. [all data]

Lacher, Billings, et al., 1952
Lacher, J.R.; Billings, T.J.; Campion, D.E., Vapor phase heats of hydrobromination of the isomeric butenes, J. Am. Chem. Soc., 1952, 74, 5291-52. [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]

Kistiakowsky, Ruhoff, et al., 1935
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. II. Hydrogenation of some simpler olefinic hydrocarbons, J. Am. Chem. Soc., 1935, 57, 876-882. [all data]

Conn, Kistiakowsky, et al., 1938
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VII. Addition of halogens to olefins, J. Am. Chem. Soc., 1938, 60, 2764-2771. [all data]

Scacchi and Back, 1977
Scacchi, G.; Back, M.H., The cycloaddition of ethylene to butene-2. II. Energy relations, Int. J. Chem. Kinet., 1977, 9, 525-534. [all data]


Notes

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