2-Butene, 2-methyl-

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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

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

2-Methyl-1-butene = 2-Butene, 2-methyl-

By formula: C5H10 = C5H10

Quantity Value Units Method Reference Comment
Δr-1.6 ± 0.72kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Methanol/H+; ALS
Δr-1.9 ± 0.33kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Ethanol/H+; ALS

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

By formula: C3H9Si+ + C5H10 = (C3H9Si+ • C5H10)

Quantity Value Units Method Reference Comment
Δr38.2kcal/molPHPMSLi and Stone, 1989gas phase; condesation; M
Quantity Value Units Method Reference Comment
Δr48.0cal/mol*KPHPMSLi and Stone, 1989gas phase; condesation; M

2-Butene, 2-methyl- + Methyl Alcohol = Butane, 2-methoxy-2-methyl-

By formula: C5H10 + CH4O = C6H14O

Quantity Value Units Method Reference Comment
Δr-7.84kcal/molEqkSerda, Izquierdo, et al., 1995liquid phase; ALS
Δr-6.41 ± 0.55kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Alcohol/alkane mixture; ALS

2-Butene, 2-methyl- + Hydrogen chloride = Butane, 2-chloro-2-methyl-

By formula: C5H10 + HCl = C5H11Cl

Quantity Value Units Method Reference Comment
Δr-14.12 ± 0.22kcal/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochloroination; ALS

2-Butene, 2-methyl- + Ethanol = Butane, 2-ethoxy-2-methyl-

By formula: C5H10 + C2H6O = C7H16O

Quantity Value Units Method Reference Comment
Δr-6.5 ± 1.6kcal/molEqkRihko, Linnekoski, et al., 1994liquid phase; solvent: Alcohol/alkane mixture; ALS

2-Butene, 2-methyl- + Trifluoroacetic acid = Acetic acid, trifluoro-, 2,2-dimethylpropyl ester

By formula: C5H10 + C2HF3O2 = C7H11F3O2

Quantity Value Units Method Reference Comment
Δr-9.11 ± 0.04kcal/molCmWiberg and Hao, 1991liquid phase; Trifluoroacetolysis; ALS

2-Butene, 2-methyl- = 1-Butene, 3-methyl-

By formula: C5H10 = C5H10

Quantity Value Units Method Reference Comment
Δr3.40 ± 0.35kcal/molEqkRadyuk, Kabo, et al., 1973gas phase; Heat of isomerization at 622 K; ALS

2-Butene, 2-methyl- = 2-Methyl-1-butene

By formula: C5H10 = C5H10

Quantity Value Units Method Reference Comment
Δr1.93 ± 0.12kcal/molEqkRadyuk, Kabo, et al., 1973gas phase; Heat of isomerization at 562 K; ALS

2-Butene, 2-methyl- + Bromine = 2,3-dibromo-2-methylbutane

By formula: C5H10 + Br2 = C5H10Br2

Quantity Value Units Method Reference Comment
Δr-30.40 ± 0.20kcal/molCmConn, Kistiakowsky, et al., 1938gas phase; At 355 °K; ALS

Hydrogen + 2-Butene, 2-methyl- = Butane, 2-methyl-

By formula: H2 + C5H10 = C5H12

Quantity Value Units Method Reference Comment
Δr-26.68 ± 0.06kcal/molChydKistiakowsky, Ruhoff, et al., 1936gas phase; ALS

2-Butene, 2-methyl- + Methyl Alcohol = Butane, 1-methoxy-2-methyl-

By formula: C5H10 + CH4O = C6H14O

Quantity Value Units Method Reference Comment
Δr-7.84 ± 0.33kcal/molEqkSerda, Izquierdo, et al., 1995liquid phase; ALS

Butane, 2-ethoxy-2-methyl- = 2-Butene, 2-methyl- + Ethanol

By formula: C7H16O = C5H10 + C2H6O

Quantity Value Units Method Reference Comment
Δr8.16 ± 0.19kcal/molEqkSharonov, Rozhnov, et al., 1995liquid 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.

Rihko, Linnekoski, et al., 1994
Rihko, L.K.; Linnekoski, J.A.; Krause, A.O., Reaction equilibria in the synthesis of 2-methoxy-2-methylbutane and 2-ethyoxy-2-methylbutane in the liquid phase, J. Chem. Eng. Data, 1994, 39, 700-704. [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]

Serda, Izquierdo, et al., 1995
Serda, J.A.; Izquierdo, J.F.; Tejero, J.; Cunill, F.; Iborra, M., Equilibrium and thermodynamics for 2-methyl-2-methoxybutane liquid-phase decomposition, Thermochim. Acta, 1995, 259, 111-120. [all data]

Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J., Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions, J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]

Wiberg and Hao, 1991
Wiberg, K.B.; Hao, S., Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols, J. Org. Chem., 1991, 56, 5108-5110. [all data]

Radyuk, Kabo, et al., 1973
Radyuk, Z.A.; Kabo, G.Ya.; Andreevskii, D.N., Isomerization equilibrium and thermodynamic properties of methylbutenes, Neftekhimiya, 1973, 13, 356-360. [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]

Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. III. Hydrogenation of some higher olefins, J. Am. Chem. Soc., 1936, 58, 137-145. [all data]

Sharonov, Rozhnov, et al., 1995
Sharonov, K.G.; Rozhnov, A.M.; Korol'kov, A.V.; Karaseva, S.Y., Enthalpies of formation of 2-methyl-2-ethoxypropane and 2-ethyl-2-ethoxypropane from equilibrium measurements, J. Chem. Thermodyn., 1995, 27, 751-753. [all data]


Notes

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