1,3,5,7-Cyclooctatetraene

• Formula: C₈H₈
• Molecular weight: 104.1491
• IUPAC Standard InChI: InChI=1S/C8H8/c1-2-4-6-8-7-5-3-1/h1-8H/b2-1-,3-1-,4-2-,5-3-,6-4-,7-5-,8-6-,8-7- Copy

  
• IUPAC Standard InChIKey: KDUIUFJBNGTBMD-BONZMOEMSA-N Copy
• CAS Registry Number: 629-20-9
• 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.
• Other names: [8]Annulene; Cyclooctatetraene; UN 2358
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry 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 compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase 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 compiled as indicated in comments:
B - John E. Bartmess
ALS - 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

C₈H₇^- +  =

By formula: C₈H₇^- + H⁺ = C₈H₈

4 +  =

By formula: 4H₂ + C₈H₈ = C₈H₁₆

=

By formula: C₈H₈ = C₈H₈

=

By formula: C₈H₈ = c₈H₈

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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

Prosen, Johnson, et al., 1950
Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heat of combustion and formation of 1,3,5,7-cyclooctatetraene and its heat of isomerization of styrene, J. Am. Chem. Soc., 1950, 72, 626-629. [all data]

Scott D.W., 1949
Scott D.W., Cyclooctatetraene: low-temperature heat capacity, heat of fusion, heat of vaporization, vapor pressure, and entropy, J. Am. Chem. Soc., 1949, 71, 1634-1636. [all data]

Dorofeeva O.V., 1986
Dorofeeva O.V., Thermodynamic properties of twenty-one monocyclic hydrocarbons, J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]

Lippincott E.R., 1951
Lippincott E.R., The thermodynamic functions of cyclooctatetraene, J. Am. Chem. Soc., 1951, 73, 3889-3891. [all data]

Springall, White, et al., 1954
Springall, H.D.; White, T.R.; Cass, R.C., Heats of combustion and molecular structure Part 1.- The resonance energy and structure of cyclo-octateraene, Trans. Faraday Soc., 1954, 50, 815. [all data]

Scott, Gross, et al., 1949
Scott, D.W.; Gross, M.E.; Oliver, G.D.; Huffman, H.M., Cycloöctatetraene: low-temperature heat capacity, heat of fusion, heat of vaporization, vapor pressure and entropy, J. Am. Chem. Soc., 1949, 71, 1634-1636. [all data]

Kato, Lee, et al., 1997
Kato, S.; Lee, H.S.; Gareyev, R.; Wenthold, P.G.; Lineberger, W.C.; DePuy, C.H.; Bierbaum, V.M., Experimental and Computational Studies of the Structures and Energetics of Cyclooctatetraene and Its Derivatives, J. Am. Chem. Soc., 1997, 119, 33, 7863, https://doi.org/10.1021/ja971433d . [all data]

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Doering, W.E.; Knox, L.H.; Mayer, J.R.; Wiley, D.W., Heats of hydrogenation. III. Hydrogenation of cycllooctatetraene and of some seven-membered non-benzenoid aromatic compounds, J. Am. Chem. Soc., 1957, 79, 4127-4133. [all data]

Prosen, Johnson, et al., 1947
Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heat of combustion and formation of 1,3,5,7-cyclooctatetraene and its heat of isomerization to styrene, J. Am. Chem. Soc., 1947, 69, 2068-2069. [all data]

Squillacote and Bergman, 1986
Squillacote, M.E.; Bergman, A., Trapping of 1,3,5,7-cyclooctatetraene valence tautomers. Thermodynamic stability of bicyclo[4.2.0]octa-2,4,7-triene, J. Org. Chem., 1986, 51, 3910-3911. [all data]

Notes

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

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  S°gas	Entropy of gas at standard conditions
  S°liquid	Entropy of liquid at standard conditions
  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
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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