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1,3,5,7-Cyclooctatetraene

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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

Quantity Value Units Method Reference Comment
Deltafgas297.6 ± 1.3kJ/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
gas326.8 ± 1.5J/mol*KN/AScott D.W., 1949GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
35.8350.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
50.68100.
66.51150.
83.80200.
112.48273.15
122.6 ± 3.5298.15
123.36300.
161.83400.
194.41500.
220.96600.
242.65700.
260.63800.
275.70900.
288.441000.
299.291100.
308.551200.
316.501300.
323.341400.
329.261500.

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
Deltafliquid254.5 ± 1.3kJ/molCmProsen, Johnson, et al., 1950ALS
Quantity Value Units Method Reference Comment
Deltacliquid-4539. ± 3.kJ/molCcbSpringall, White, et al., 1954Corresponding «DELTA»fliquid = 248. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-4545.92 ± 0.92kJ/molCmProsen, Johnson, et al., 1950Corresponding «DELTA»fliquid = 254.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid220.29J/mol*KN/AScott, Gross, et al., 1949DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
185.18298.15Scott, Gross, et al., 1949T = 12 to 340 K.; DH

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil415.7KN/AAldrich Chemical Company Inc., 1990BS
Tboil416.KN/AReppe, Schlichting, et al., 1948Uncertainty assigned by TRC = 4. K; TRC
Quantity Value Units Method Reference Comment
Tfus265.0KN/ACope and Bailey, 1948Uncertainty assigned by TRC = 1.5 K; TRC
Tfus266.KN/AReppe, Schlichting, et al., 1948Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Ttriple268.48KN/AScott, Gross, et al., 1949, 2Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Deltavap43.1 ± 0.31kJ/molVScott, Gross, et al., 1949, 3ALS
Deltavap43.1kJ/molN/AScott, Gross, et al., 1949AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
43.9288.AStephenson and Malanowski, 1987Based on data from 273. - 348. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
273. - 348.3.99581402.263-63.521Scott, Gross, et al., 1949Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
11.2742268.48Scott, Gross, et al., 1949DH
11.25268.5Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
41.493268.48Scott, Gross, et al., 1949DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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
Deltar1601. ± 12.kJ/molG+TSKato, Lee, et al., 1997gas phase; B
Quantity Value Units Method Reference Comment
Deltar1568. ± 10.kJ/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-409.9 ± 0.2kJ/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-143.7 ± 1.4kJ/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
Deltar23. ± 3.kJ/molEqkSquillacote and Bergman, 1986gas phase; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

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


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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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
NIST MS number 1259

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

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]

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

Reppe, Schlichting, et al., 1948
Reppe, W.; Schlichting, O.; Klager, K.; Toepel, T., Cyclizing Polymerization of Acetylene I. Cyclooctatetraene, Justus Liebigs Ann. Chem., 1948, 560, 1-92. [all data]

Cope and Bailey, 1948
Cope, A.C.; Bailey, W.J., Cyclic Polyolefins II. Synthesis of Cyclooctatetraene from Chloroprene, J. Am. Chem. Soc., 1948, 70, 2305. [all data]

Scott, Gross, et al., 1949, 2
Scott, D.W.; Gross, M.E.; Oliver, G.D.; Huffman, H.M., Cyclooctatetraene: low-temperature heat capacity, heat of fusion, heat of vaporization, vapor pressure and entropy, J. Am. Chem. Soc., 1949, 71, 1634. [all data]

Scott, Gross, et al., 1949, 3
Scott, D.W.; Gross, M.E.; Oliver, G.D.; Huffman, H.M., Cyclooctatetraene: Low-temperature heat capacity, heat of fusion, heat of vaporization, vapor pressure and entropy, J. Am. Chem. Soc., 1949, 71, 1634-16. [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]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References