1,3,5-Hexatriene, (Z)-

• Formula: C₆H₈
• Molecular weight: 80.1277
• IUPAC Standard InChI: InChI=1S/C6H8/c1-3-5-6-4-2/h3-6H,1-2H2/b6-5- Copy

  
• IUPAC Standard InChIKey: AFVDZBIIBXWASR-WAYWQWQTSA-N Copy
• CAS Registry Number: 2612-46-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Stereoisomers:
  • 1,3,5-Hexatriene
  • 1,3,5-Hexatriene, (E)-
• Other names: (Z)-1,3,5-Hexatriene; cis-Hexatriene; cis-1,3,5-Hexatriene; 1,3,5-Hexatriene, cis-; (Z)-CH2=CHCH=CHCH=CH2
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

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

3 +  =

By formula: 3H₂ + C₆H₈ = C₆H₁₄

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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₆H₈⁺ (ion structure unspecified)

Ionization energy determinations

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

References

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

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Sondheimer, Ben-Efraim, et al., 1961
Sondheimer, F.; Ben-Efraim, D.A.; Wolovsky, R., Unsaturated Macrocyclic Compounds XVII. The Prototropic Rearrangement of Linear 1,5-Enynes to COnjugated Polyenes. The Synthesis of A Series of Vinylogs of Butadiene, J. Am. Chem. Soc., 1961, 83, 1675-81. [all data]

Hwa, De Benneville, et al., 1960
Hwa, J.C.H.; De Benneville, P.L.; Sims, H.J., A New Preparation of 1,3,5-Hexatriene and the Separation of Its Geometrical Isomers, J. Am. Chem. Soc., 1960, 82, 2537-40. [all data]

Farmer, Laroiz, et al., 1927
Farmer, E.H.; Laroiz, B.D.; Switz, T.M.; Thorpe, J.F., Properties of Conjugated Compounds Part III. The Bearing of Hexatriene Chemistry on the Reactive Forms of Conjugated Hydrocarbons, J. Chem. Soc., 1927, 1927, 2937-58. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Letcher and Marsicano, 1974
Letcher, T.M.; Marsicano, F., Vapour pressures and densities of some unsaturated C6 acyclic and cyclic hydrocarbons between 300 and 320 K, The Journal of Chemical Thermodynamics, 1974, 6, 5, 509-514, https://doi.org/10.1016/0021-9614(74)90013-5 . [all data]

Turner, Mallon, et al., 1973
Turner, R.B.; Mallon, B.J.; Tichy, M.; Doering, W.v.E.; Roth, W.R.; Schroder, G., Heats of hydrogenation. X. Conjugative interaction in cyclic dienes and trienes, J. Am. Chem. Soc., 1973, 95, 8605-8610. [all data]

Allan, Dannacher, et al., 1980
Allan, M.; Dannacher, J.; Maier, J.P., Radiative and fragmentation decay of the cations of trans- and cis 1,3,5-hexatriene of all trans-1,3,5-heptatriene in the A(π^-1) states, studied by emission photoelectron-photoion coincidence spectroscopy, J. Chem. Phys., 1980, 73, 3114. [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]

Gavin and Rice, 1974
Gavin, R.M., Jr.; Rice, S.A., Spectroscopic properties of polyenes. II. The vacuum ultraviolet spectra of cis- and trans-1,3,5-hexatriene, J. Chem. Phys., 1974, 60, 3231. [all data]

Beez, Bieri, et al., 1973
Beez, M.; Bieri, G.; Bock, H.; Heilbronner, E., The ionization potentials of butadiene, hexatriene, andtheir methyl derivatives: evidence for through space interaction between double bond π-orbitals and non-bonded pseudo-π orbitals of methyl groups?, Helv. Chim. Acta, 1973, 56, 1028. [all data]

Notes

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• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Tboil	Boiling point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization

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