2-Butene, (E)-

• Formula: C₄H₈
• Molecular weight: 56.1063
• IUPAC Standard InChI: InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3/b4-3+ Copy

  
• IUPAC Standard InChIKey: IAQRGUVFOMOMEM-ONEGZZNKSA-N Copy
• CAS Registry Number: 624-64-6
• 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:
  • (E)-2-Butene-d8
• Stereoisomers:
  • 2-Butene
  • 2-Butene, (Z)-
• Other names: (E)-2-Butene; trans-Butene; trans-1,2-Dimethylethylene; trans-2-Butene; 2-trans-Butene; (E)-2-C4H8; 2-Butene, trans-; Butene-2,trans; t-Butene-2; (E)-but-2-ene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Electron-Impact Ionization Cross Sections (on physics web site)
  • Gas Phase Kinetics Database
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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 by: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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

=

By formula: C₄H₈ = C₄H₈

=

By formula: C₄H₈ = C₄H₈

 +  =

By formula: HBr + C₄H₈ = C₄H₉Br

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

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

 +  =

By formula: H₂ + C₄H₈ = C₄H₁₀

 +  =

By formula: C₄H₈ + Br₂ = C₄H₈Br₂

=  + 

By formula: C₄H₉Cl = C₄H₈ + HCl

 +  =

By formula: C₄H₈ + C₂H₄ = C₆H₁₂

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:
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 C₄H₈⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

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.

Chao, Hall, et al., 1983
Chao, J.; Hall, K.R.; Yao, J.M., Thermodynamic properties of simple alkenes, Thermochim. Acta, 1983, 64(3), 285-303. [all data]

Guttman and Pitzer, 1945
Guttman, L.; Pitzer, K.S., trans-2-Butene. The heat capacity, heats of fusion and vaporization, and vapor pressure. The entropy and barrier to internal rotation, J. Am. Chem. Soc., 1945, 67, 324-327. [all data]

Todd and Parks, 1936
Todd, S.S.; Parks, G.S., Thermal data on organic compounds. XV. Some heat capacity, entropy and free energy data for the isomeric butenes, J. Am. Chem. Soc., 1936, 58, 134-137. [all data]

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]

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]

Traeger, 1986
Traeger, J.C., Heat of formation for the 1-methylallyl cation by photoionization mass spectrometry, J. Phys. Chem., 1986, 90, 4114. [all data]

Wood and Taylor, 1979
Wood, K.V.; Taylor, J.W., A photoionization mass spectrometric study of autoionization in ethylene and trans-2-butene, Int. J. Mass Spectrom. Ion Phys., 1979, 30, 307. [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]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Clary, Lewis, et al., 1974
Clary, D.C.; Lewis, A.A.; Morland, D.; Murrell, J.N.; Heilbronner, E., Ionization potentials of cycloalkenes, J. Chem. Soc. Faraday Trans. 2, 1974, 70, 1889. [all data]

Masclet, Grosjean, et al., 1973
Masclet, P.; Grosjean, D.; Mouvier, G., Alkene ionization potentials. Part I. Quantitative determination of alkyl group structural effects, J. Electron Spectrosc. Relat. Phenom., 1973, 2, 225. [all data]

Frost and Sandhu, 1971
Frost, D.C.; Sandhu, J.S., Ionization potentials of ethylene and some methyl-substituted ethylenes as determined by photoelectron spectroscopy, Indian J. Chem., 1971, 9, 1105. [all data]

McDiarmid, 1969
McDiarmid, R., Rydberg progressions in cis- and trans-butene, J. Chem. Phys., 1969, 50, 2328. [all data]

Haselbach, Hashmall, et al., 1969
Haselbach, E.; Hashmall, J.A.; Heilbronner, E.; Hornung, V., The interaction between the lone pairs in azomethane, Angew. Chem. Intern. Ed., 1969, 8, 878. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [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]

Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C., The effect of fluorine on the electronic spectra and ionization potentials of molecules, Proc. Roy. Soc. (London), 1960, A258, 459. [all data]

Kimura, Katsumata, et al., 1975
Kimura, K.; Katsumata, S.; Yamazaki, T.; Wakabayashi, H., UV photoelectron spectra and sum rule consideration; out-of-plane orbitals of unsaturated compounds with planar-skeleton structure, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 41. [all data]

White, Carlson, et al., 1974
White, R.M.; Carlson, T.A.; Spears, D.P., Angular distribution of the photoelectron spectra for ethylene, propylene, butene and butadiene, J. Electron Spectrosc. Relat. Phenom., 1974, 3, 59. [all data]

Robin, Taylor, et al., 1973
Robin, M.B.; Taylor, G.N.; Kuebler, N.A.; Bach, R.D., Planarity of the carbon skeleton in various alkylated olefins, J. Org. Chem., 1973, 38, 1049. [all data]

Brundle, Robin, et al., 1972
Brundle, C.R.; Robin, M.B.; Kuebler, N.A.; Basch, H., Perfluoro effect in photoelectron spectroscopy. I. Nonaromatic molecules, J. Am. Chem. Soc., 1972, 94, 1451. [all data]

Meisels, Park, et al., 1970
Meisels, G.G.; Park, J.Y.; Giessner, B.G., Ionization and dissociation of C₄H₈ isomers, J. Am. Chem. Soc., 1970, 92, 254. [all data]

Traeger, 1984
Traeger, J.C., A study of the allyl cation thermochemistry by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  S°liquid	Entropy of liquid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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