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
Δfgas71.13 ± 0.31kcal/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
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
Δfliquid60.82 ± 0.32kcal/molCmProsen, Johnson, et al., 1950ALS
Quantity Value Units Method Reference Comment
Δcliquid-1084.9 ± 0.7kcal/molCcbSpringall, White, et al., 1954Corresponding Δfliquid = 59.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-1086.50 ± 0.22kcal/molCmProsen, Johnson, et al., 1950Corresponding Δfliquid = 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

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
Δvap10.3 ± 0.075kcal/molVScott, Gross, et al., 1949, 3ALS
Δvap10.3kcal/molN/AScott, Gross, et al., 1949AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
10.5288.AStephenson and Malanowski, 1987Based on data from 273. to 348. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
273. to 348.3.99011402.263-63.521Scott, Gross, et al., 1949Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.69460268.48Scott, Gross, et al., 1949DH
2.689268.5Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
9.9171268.48Scott, 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
Δr382.7 ± 2.8kcal/molG+TSKato, Lee, et al., 1997gas phase; B
Quantity Value Units Method Reference Comment
Δr374.8 ± 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
Δr-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
Δr-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
Δr5.5 ± 0.6kcal/molEqkSquillacote and Bergman, 1986gas phase; ALS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

View reactions leading to C8H8+ (ion structure unspecified)

Electron affinity determinations

EA (eV) Method Reference Comment
0.570 ± 0.030N/AMiller, Viggiano, et al., 2002B
0.550 ± 0.020IMREKato, Lee, et al., 1997B
0.650 ± 0.043LPESWenthold, Hrovat, et al., 1996EA(D4h COT) = 1.099 ± 0.01 eV. D4H is TS, 10-11 kcal/mol above GS D8h; B
0.58 ± 0.10CIDCDenault, Chen, et al., 1998entropy of attachment: -14.7±13 eu; B
<0.823919PDGygax, Peters, et al., 1979B
0.577 ± 0.043ECDWentworth and Ristau, 1969B

Ionization energy determinations

IE (eV) Method Reference Comment
8.03PEFu and Dunbar, 1978LLK
8.0PEBatich, Bischof, et al., 1973LLK
8.21PEDewar, Harget, et al., 1969Unpublished result of M.J.S. Dewar and S.D. Worley; RDSH
8.04PEAl-Joboury and Turner, 1964RDSH
7.99 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
8.43PEFu and Dunbar, 1978Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.40 ± 0.10?EIFranklin and Carroll, 1969RDSH
C4H2+17.11 ± 0.102C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H3+18.16 ± 0.252C2H2+HEIFranklin and Carroll, 1969RDSH
C4H4+15.10 ± 0.102C2H2EIFranklin and Carroll, 1969RDSH
C5H3+16.41 ± 0.15C2H2+CH3?EIFranklin and Carroll, 1969RDSH
C6H5+14.58 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C6H6+9.4 ± 0.05C2H2TRPILifshitz and Malinovich, 1984LBLHLM
C6H6+9.70 ± 0.12C2H2EIFranklin and Carroll, 1969RDSH
C8H6+11.70 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C8H7+10.90 ± 0.10HEIFranklin and Carroll, 1969RDSH

De-protonation reactions

C8H7- + Hydrogen cation = 1,3,5,7-Cyclooctatetraene

By formula: C8H7- + H+ = C8H8

Quantity Value Units Method Reference Comment
Δr382.7 ± 2.8kcal/molG+TSKato, Lee, et al., 1997gas phase; B
Quantity Value Units Method Reference Comment
Δr374.8 ± 2.5kcal/molIMREKato, Lee, et al., 1997gas phase; B

IR Spectrum

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

Miller, Viggiano, et al., 2002
Miller, T.M.; Viggiano, A.A.; Miller, A.E.S., Electron attachment and detachment: Cyclooctatetraene, J. Phys. Chem. A, 2002, 106, 43, 10200-10204, https://doi.org/10.1021/jp0205214 . [all data]

Wenthold, Hrovat, et al., 1996
Wenthold, P.G.; Hrovat, D.A.; Borden, W.T.; Lineberger, W.C., Transition State Spectroscopy of Cyclooctatetraene, Science, 1996, 272, 5267, 1456, https://doi.org/10.1126/science.272.5267.1456 . [all data]

Denault, Chen, et al., 1998
Denault, J.W.; Chen, G.D.; Cooks, R.G., Electron affinity of 1,3,5,7-cyclooctatetraene determined by the kinetic method, J. Am. Soc. Mass Spectrom., 1998, 9, 11, 1141-1145, https://doi.org/10.1016/S1044-0305(98)00092-0 . [all data]

Gygax, Peters, et al., 1979
Gygax, R.; Peters, H.L.; Brauman, J.I., Photodetachment of electrons from anions of high symmetry. Electron photodetachment spectra of the cycloctatetraenyl and perinaphthenyl anions, J. Am. Chem. Soc., 1979, 101, 2567. [all data]

Wentworth and Ristau, 1969
Wentworth, W.E.; Ristau, W., Thermal Electron Attachment Involving a Change in Molecular Geometry, J. Phys. Chem., 1969, 73, 7, 2126, https://doi.org/10.1021/j100727a005 . [all data]

Fu and Dunbar, 1978
Fu, E.W.; Dunbar, R.C., Photodissociation spectroscopy and structural rearrangements in ions of cyclooctatetraene, styrene and related molecules, J. Am. Chem. Soc., 1978, 100, 2283. [all data]

Batich, Bischof, et al., 1973
Batich, C.; Bischof, P.; Heilbronner, E., The photoelectron spectra of cyclooctatetraene and its hydrogenated derivatives, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 333. [all data]

Dewar, Harget, et al., 1969
Dewar, M.J.S.; Harget, A.; Haselbach, E., Cyclooctatetraene and ions derived from it, J. Am. Chem. Soc., 1969, 91, 7521. [all data]

Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W., Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials, J. Chem. Soc., 1964, 4434. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R., The effect of molecular structure on ionic decomposition. I. An electron impact study of seven C8H8 isomers, J. Am. Chem. Soc., 1969, 91, 5940. [all data]

Lifshitz and Malinovich, 1984
Lifshitz, C.; Malinovich, Y., Time resolved photoionization mass spectrometry in the millisecond range, Int. J. Mass Spectrom. Ion Processes, 1984, 60, 99. [all data]


Notes

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