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
Δfgas297.6 ± 1.3kJ/molN/AProsen, Johnson, et al., 1950Value computed using ΔfHliquid° value of 254.5±1.3 kj/mol from Prosen, Johnson, et al., 1950 and ΔvapH° 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
Δfliquid254.5 ± 1.3kJ/molCmProsen, Johnson, et al., 1950ALS
Quantity Value Units Method Reference Comment
Δcliquid-4539. ± 3.kJ/molCcbSpringall, White, et al., 1954Corresponding Δfliquid = 248. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-4545.92 ± 0.92kJ/molCmProsen, Johnson, et al., 1950Corresponding Δfliquid = 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
Δvap43.1 ± 0.31kJ/molVScott, Gross, et al., 1949, 3ALS
Δvap43.1kJ/molN/AScott, Gross, et al., 1949AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
43.9288.AStephenson and Malanowski, 1987Based on data from 273. to 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. to 348.3.99581402.263-63.521Scott, Gross, et al., 1949Coefficents calculated by NIST from author's data.

Enthalpy of fusion

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

Entropy of fusion

ΔfusS (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
Δr1601. ± 12.kJ/molG+TSKato, Lee, et al., 1997gas phase; B
Quantity Value Units Method Reference Comment
Δr1568. ± 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
Δr-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
Δr-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
Δr23. ± 3.kJ/molEqkSquillacote and Bergman, 1986gas phase; ALS

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySqualane70.850.Schomburg, 1966 

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
PackedSE-30880.Buchman, Cao, et al., 1984He, Chromosorb AW, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
PackedSE-30880.Peng, Ding, et al., 1988Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min)

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryCarbowax 20M1244.Verzera, Campisi, et al., 200560. m/0.25 mm/0.25 μm, He, 45. C @ 0.17 min, 2. K/min; Tend: 250. C
CapillaryCP-Wax 52CB1244.Verzera, Campisi, et al., 200160. m/0.25 mm/0.25 μm, He, 45. C @ 0.17 min, 2. K/min; Tend: 250. C
CapillaryDB-Wax1264.Shimoda, Peralta, et al., 199660. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 50. C; Tend: 230. C
PackedCarbowax 20M1226.Buchman, Cao, et al., 1984He, Supelcoport, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryCP Sil 8 CB894.Wang and Guo-Y. -L., 200430. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 10. K/min, 200. C @ 2. min

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillarySqualane850.Chen, 2008Program: not specified
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.880.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
PackedSE-30889.Robinson and Odell, 1971N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold)
PackedSqualane846.Robinson and Odell, 1971N2, Embacel; Column length: 3.0 m; Program: 25C(5min) => 2C/min => 35 => 4C/min => 95C(hold)

Normal alkane RI, polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryCarbowax 20M1244.Editorial paper, 2005Program: not specified
CapillaryDB-Wax1199.Peng, Yang, et al., 1991Program: not specified
CapillaryCarbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc.1226.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, 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]

Schomburg, 1966
Schomburg, G., Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe, J. Chromatogr., 1966, 23, 18-41, https://doi.org/10.1016/S0021-9673(01)98653-4 . [all data]

Buchman, Cao, et al., 1984
Buchman, O.; Cao, G.-Y.; Peng, C.T., Structure assignment by retention index in gas-liquid radiochromatography of substituted cyclohexenes, J. Chromatogr., 1984, 312, 75-90, https://doi.org/10.1016/S0021-9673(01)92765-7 . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Verzera, Campisi, et al., 2005
Verzera, A.; Campisi, S.; Zappalá, M., SUPELCO. Using SPME-GC-MS to characterize volatile components of honey as indicators of botanical origin, 2005, retrieved from http://www.sigmaaldrich.com/Brands/SupelcoHome/TheReporter.html. [all data]

Verzera, Campisi, et al., 2001
Verzera, A.; Campisi, S.; Zappalá, M.; Bonaccorsi, I., SPME-GC-MS analysis of honey volatile components for the characterization of different floral origin, Am. Lab. Fairfield Conn., 2001, 33, 15, 18-21. [all data]

Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y., Headspace gas analysis of fish sauce, J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u . [all data]

Wang and Guo-Y. -L., 2004
Wang, H.-Y.; Guo-Y. -L., Rapid analysis of the volatile compounds in the rhizomes of Rhodiola sachalinensis and Rhodiola sacra by static headspace-gas chromatography-tandem mass spectrometry, Anal. Letters, 2004, 37, 10, 2151-2161, https://doi.org/10.1081/AL-200026690 . [all data]

Chen, 2008
Chen, H.-F., Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression, Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Robinson and Odell, 1971
Robinson, P.G.; Odell, A.L., A system of standard retention indices and its uses. The characterisation of stationary phases and the prediction of retention indices, J. Chromatogr., 1971, 57, 1-10, https://doi.org/10.1016/0021-9673(71)80001-8 . [all data]

Editorial paper, 2005
Editorial paper, Solid Phase Microextraction (SPME) Application Guide, The Reporter Europe (Supelco), 2005, 16, 5, 12-12. [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]


Notes

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