1,5-Cyclooctadiene, (Z,Z)-

• Formula: C₈H₁₂
• Molecular weight: 108.1809
• IUPAC Standard InChI: InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7- Copy

  
• IUPAC Standard InChIKey: VYXHVRARDIDEHS-QGTKBVGQSA-N Copy
• CAS Registry Number: 1552-12-1
• 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.
• Stereoisomers:
  • 1,5-Cyclooctadiene
  • 1,5-Cyclooctadiene, (E,E)-
  • 1,5-Cyclooctadiene, (E,Z)-
• Other names: (Z,Z)-1,5-Cyclooctadiene; cis,cis-1,5-Cyclooctadiene; COD; cis,cis-Cycloocta-1,5-diene; 1,5-Cyclooctadiene; (Z,Z)-cycloocta-1,5-diene
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• 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

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: 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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: José A. Martinho Simões

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

C₁₈H₂₇ClRu (solution) +  (solution) = C₁₆H₃₁ClP₂Ru (solution) +  (solution)

By formula: C₁₈H₂₇ClRu (solution) + C₁₀H₁₅NO₂ (solution) = C₁₆H₃₁ClP₂Ru (solution) + C₈H₁₂ (solution)

 (solution) = 2 (solution) +  (cr)

By formula: (Ni(C₈H₁₂)₂) (solution) = 2C₈H₁₂ (solution) + Ni (cr)

 (solution) +  (solution) = C₁₃H₁₉O₂Rh (solution) + 2 (solution)

By formula: C₉H₁₅O₂Rh (solution) + C₈H₁₂ (solution) = C₁₃H₁₉O₂Rh (solution) + 2C₂H₄ (solution)

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.

Kozina, Timofeeva, et al., 1976
Kozina, M.P.; Timofeeva, L.P.; Gal'chenko, G.L.; Gvozdeva, E.A.; Cherednichenko, V.M., The determination of the enthalphy of combustion of cis, cis-cyclooctadiene-1,5, Termodin. Org. Soedin., 1976, 9-11. [all data]

Rauh, Geyer, et al., 1973
Rauh, H.J.; Geyer, W.; Schmidt, H.; Geiseler, G., Bildungsenthalpien und mesomerieenergien von π-bindungssystemen, Z. Phys. Chem. (Leipzig), 1973, 253, 43-48. [all data]

Treboganov, Mitsner, et al., 1965
Treboganov, A.D.; Mitsner, B.I.; Zinkevich, E.P.; Kraevskii, A.A.; Preobrazhenskii, N.A., Macrocyclic compounds. I. Synthesis of cyclooctane and cyclododecane, Zh. Organ. Khim., 1965, 1, 1583-6. [all data]

Zakharkin and Zhigareva, 1963
Zakharkin, L.I.; Zhigareva, G.G., Dimerization of butadiene to cis-cis-1,5-cyclooctadiene catalyzed by pi-complex compounds of nickel, Izv. Akad. Nauk SSSR, 1963, Otd. Khim. Nauk 386 1963 1963. [all data]

Ziegler and Wilms, 1948
Ziegler, K.; Wilms, H., Stereoisomerism of Eight-membered Cycloolefin Rings, Naturwissenschaften, 1948, 35, 157-8. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Varushchenko, Pashchenko, et al., 1996
Varushchenko, R.M.; Pashchenko, L.L.; Druzhinina, A.I., Enthalpies of vaporization of some mono- and polycyclic hydrocarbons, Zh. Fiz. Khim., 1996, 70, 2, 228. [all data]

Luo, Zhu, et al., 1994
Luo, L.; Zhu, N.; Zhu, N.-J.; Stevens, E.D.; Nolan, S.P.; Fagan, P.J., Organometallics, 1994, 13, 669. [all data]

Luo, Nolan, et al., 1993
Luo, L.; Nolan, S.P.; Fagan, P.J., Organometallics, 1993, 12, 4305. [all data]

Tolman, Reutter D.W., et al., 1976
Tolman, C.A.; Reutter D.W.; Seidel, W.C., J. Organometal. Chem., 1976, 117, C30. [all data]

Jesse, Cordfunke, et al., 1979
Jesse, A.C.; Cordfunke, E.H.P.; Ouweltjes, W., Thermochim. Acta, 1979, 30, 293. [all data]

Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

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