2,4-Hexadiene, (E,Z)-

• Formula: C₆H₁₀
• Molecular weight: 82.1436
• IUPAC Standard InChI: InChI=1S/C6H10/c1-3-5-6-4-2/h3-6H,1-2H3/b5-3-,6-4+ Copy

  
• IUPAC Standard InChIKey: APPOKADJQUIAHP-CIIODKQPSA-N Copy
• CAS Registry Number: 5194-50-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Stereoisomers:
  • 2,4-Hexadiene, (E,E)-
  • 2,4-Hexadiene
  • (Z),(Z)-2,4-Hexadiene
• Other names: (E),(Z)-CH3CH=CHCH=CHCH3; cis,trans-2,4-Hexadiene; (E,Z)-2,4-Hexadiene; (Z,E)-2,4-Hexadiene; cis,trans-hexa-2,4-diene
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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: C₆H₁₀ = C₆H₁₀

2 +  =

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

=

By formula: C₆H₁₀ = C₆H₁₀

=

By formula: C₆H₁₀ = C₆H₁₀

=

By formula: C₆H₁₀ = C₆H₁₀

=

By formula: C₆H₁₀ = C₆H₁₀

Gas phase ion energetics 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₆H₁₀⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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Additional Data

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

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

Fang and Rogers, 1992
Fang, W.; Rogers, D.W., Enthalpy of hydrogenation of the hexadienes and cis- and trans-1,3,5-hexatriene, J. Org. Chem., 1992, 57, 2294-2297. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Anonymous, 1963
Anonymous, R., , E. I. Du Pont, 1963. [all data]

Buechele, Weitz, et al., 1984
Buechele, J.L.; Weitz, E.; Lewis, F.D., Laser-induced infrared multiphoton isomerization reactions of 2,4- and 1,3-hexadienes, J. Phys. Chem., 1984, 88, 868-876. [all data]

Petrova-Kuminskaya, Roganov, et al., 1984
Petrova-Kuminskaya, S.V.; Roganov, G.N.; Kabo, G.Ya., Enthalpies of formation and isomerization of alkadienes, Probl. Kalorim. Khim. Termodin., Dokl. Vses. Konf., 10th, 1984, 1, 234-236. [all data]

Petrova-Kuminskaya, Baranov, et al., 1983
Petrova-Kuminskaya, S.V.; Baranov, O.M.; Roganov, G.N.; Kabo, G.Ya., Equilibrium and thermodynamics of the isomerization of hexadienes, Neftekhimiya, 1983, 23, 489-494. [all data]

Wolkoff, Holmes, et al., 1980
Wolkoff, P.; Holmes, J.L.; Lossing, F.P., On the formation of cyclopentenium cations from all C₆H₁₀⁺ molecular ion structures, Can. J. Chem., 1980, 58, 251. [all data]

Rucker, Lang, et al., 1980
Rucker, C.; Lang, D.; Sauer, J.; Friege, H.; Sustmann, R., Reaktivitat substituierter 1,3-Butadiene in Diels-Alder-Reaktionen, Chem. Ber., 1980, 113, 1663. [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]

Masclet, Mouvier, et al., 1981
Masclet, P.; Mouvier, G.; Bocquet, J.F., Effets electroniques et effets steriques dus a la substitution alcoyle dans les dienes conjugues, J. Chim. Phys., 1981, 78, 99. [all data]

Safina, Poznyak, et al., 1989
Safina, L.R.; Poznyak, T.I.; Lisitsyn, D.M.; Kiseleva, E.V.; Kovalev, G.I., Selective gas-chromatographic determination of trace unsaturated and aromatic-hydrocarbons in complex-mixtures, J. Appl. Chem. USSR (Engl. Transl.), 1989, 44, 5, 749-754. [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Xu, van Stee, et al., 2003
Xu, X.; van Stee, L.L.P.; Williams, J.; Beens, J.; Adahchour, M.; Vreuls, R.J.J.; Brinkman, U.A.Th.; Lelieveld, J., Comprehensive two-dimensional gas chromatography (GC×GC) measurements of volatile organic compounds in the atmosphere, Atmos. Chem. Phys., 2003, 3, 3, 665-682, https://doi.org/10.5194/acp-3-665-2003 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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