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1,3,5,7-Cyclooctatetraene

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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:
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas71.13 ± 0.31kcal/molN/AProsen, Johnson, et al., 1950Value computed using «DELTA»fHliquid° value of 254.5±1.3 kj/mol from Prosen, Johnson, et al., 1950 and «DELTA»vapH° value of 43.1±0.31 kj/mol from missing citation.; DRB
Quantity Value Units Method Reference Comment
gas78.10 ± 0.35cal/mol*KN/AScott D.W., 1949GT

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
8.56450.Dorofeeva O.V., 1986Selected values of Cp(T) are in close agreement with those calculated by [ Lippincott E.R., 1951], while the S(T) values are 1.5-2.0 J/mol*K larger than obtained by [ Lippincott E.R., 1951].; GT
12.11100.
15.90150.
20.03200.
26.883273.15
29.30 ± 0.84298.15
29.484300.
38.678400.
46.465500.
52.811600.
57.995700.
62.292800.
65.894900.
68.9391000.
71.5321100.
73.7451200.
75.6451300.
77.2801400.
78.6951500.

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

Quantity Value Units Method Reference Comment
Deltafliquid60.82 ± 0.32kcal/molCmProsen, Johnson, et al., 1950ALS
Quantity Value Units Method Reference Comment
Deltacliquid-1084.9 ± 0.7kcal/molCcbSpringall, White, et al., 1954Corresponding «DELTA»fliquid = 59.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-1086.50 ± 0.22kcal/molCmProsen, Johnson, et al., 1950Corresponding «DELTA»fliquid = 60.83 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid52.651cal/mol*KN/AScott, Gross, et al., 1949DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
44.259298.15Scott, Gross, et al., 1949T = 12 to 340 K.; DH

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:
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- + Hydrogen cation = 1,3,5,7-Cyclooctatetraene

By formula: C8H7- + H+ = C8H8

Quantity Value Units Method Reference Comment
Deltar382.7 ± 2.8kcal/molG+TSKato, Lee, et al., 1997gas phase; B
Quantity Value Units Method Reference Comment
Deltar374.8 ± 2.5kcal/molIMREKato, Lee, et al., 1997gas phase; B

4Hydrogen + 1,3,5,7-Cyclooctatetraene = Cyclooctane

By formula: 4H2 + C8H8 = C8H16

Quantity Value Units Method Reference Comment
Deltar-97.96 ± 0.05kcal/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid; ALS

1,3,5,7-Cyclooctatetraene = Styrene

By formula: C8H8 = C8H8

Quantity Value Units Method Reference Comment
Deltar-34.35 ± 0.34kcal/molCisoProsen, Johnson, et al., 1947liquid phase; ALS

1,3,5,7-Cyclooctatetraene = Bicyclo[4.2.0]octa-2,4,7-triene

By formula: C8H8 = c8H8

Quantity Value Units Method Reference Comment
Deltar5.5 ± 0.6kcal/molEqkSquillacote and Bergman, 1986gas phase; ALS

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

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