1,5-Cyclooctadiene

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas13.7 ± 0.7kcal/molCcbLebedev, Tsvetkova, et al., 1975Heat of formtion values corrected; Author's hf298_liquid=7.6±0.7 kcal/mol; ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
9.04950.Dorofeeva O.V., 1986The value of S(298.15 K) calculated by molecular mechanics method [ Ermer O., 1976] is about 2 J/mol*K lower than that selected here.; GT
12.76100.
17.08150.
21.94200.
30.096273.15
33.1 ± 1.4298.15
33.277300.
44.935400.
55.198500.
63.714600.
70.722700.
76.530800.
81.386900.
85.4801000.
88.9481100.
91.9051200.
94.4341300.
96.6061400.
98.4801500.

Condensed phase thermochemistry data

Go To: Top, Gas 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:
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
Δfliquid5.8 ± 0.7kcal/molCcbLebedev, Tsvetkova, et al., 1975Heat of formtion values corrected; Author's hf298_liquid=7.6±0.7 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-1168.1 ± 0.7kcal/molCcbLebedev, Tsvetkova, et al., 1975Heat of formtion values corrected; Author's hf298_liquid=7.6±0.7 kcal/mol; Corresponding Δfliquid = 5.8 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid59.75cal/mol*KN/ALebedev, Lebedev, et al., 1975DH
liquid63.17cal/mol*KN/ALebedev, Tsvetkova, et al., 1975, 2DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
47.54298.15Lebedev, Lebedev, et al., 1975T = 6 to 320 K.; DH
49.74298.15Lebedev, Tsvetkova, et al., 1975, 2T = 10.6 to 322.7 K. Data deposited in VINITI, No. 1324-75, 15 May 1975.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil422.7KN/AAldrich Chemical Company Inc., 1990BS
Tboil422.KN/ACope and Bailey, 1948Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Tfus203.80KN/AOtt, Goates, et al., 1974Uncertainty assigned by TRC = 0.06 K; TRC
Tfus204.KN/ACope, Stevens, et al., 1950Uncertainty assigned by TRC = 4. K; TRC
Tfus201.KN/ACope, Stevens, et al., 1950Uncertainty assigned by TRC = 4. K; TRC
Quantity Value Units Method Reference Comment
Ttriple203.980KN/ALebedev, Lebedev, et al., 1975, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Δvap7.89kcal/molN/ALebedev, Tsvetkova, et al., 1975DRB

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
11.5194.4Domalski and Hearing, 1996CAL

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
-0.0939194.3crystaline, IIcrystaline, ILebedev, Lebedev, et al., 1975DH
2.349203.983crystaline, IliquidLebedev, Lebedev, et al., 1975DH
-0.0911194.34crystaline, IIcrystaline, ILebedev, Tsvetkova, et al., 1975, 2Irreversible exothermic transition.; DH
2.349203.983crystaline, IliquidLebedev, Tsvetkova, et al., 1975, 2DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
11.53203.983crystaline, IliquidLebedev, Lebedev, et al., 1975DH
11.53203.983crystaline, IliquidLebedev, Tsvetkova, et al., 1975, 2DH

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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 by: 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

1,5-Cyclooctadiene + 2Hydrogen = Cyclooctane

By formula: C8H12 + 2H2 = C8H16

Quantity Value Units Method Reference Comment
Δr-55.0 ± 0.1kcal/molChydRoth, Adamczak, et al., 1991liquid phase
Δr-53.68 ± 0.02kcal/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Glacial acetic acid

1,5-Cyclooctadiene = 1,3-Cyclooctadiene, (Z,Z)-

By formula: C8H12 = C8H12

Quantity Value Units Method Reference Comment
Δr-4.6 ± 0.2kcal/molEqkTaskinen and Nummelin, 1985liquid phase

1,5-Cyclooctadiene = 1,4-Cyclooctadiene, (Z,Z)-

By formula: C8H12 = C8H12

Quantity Value Units Method Reference Comment
Δr-0.7 ± 0.2kcal/molEqkTaskinen and Nummelin, 1985liquid phase

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)

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

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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

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.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 886
NIST MS number 228933

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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.

Lebedev, Tsvetkova, et al., 1975
Lebedev, B.V.; Tsvetkova, L.Ya.; Kiparisova, E.G.; Lebedev, N.K., Thermodynamic properties of cyclo-octa-1,5-diene, Russ. J. Phys. Chem. (Engl. Transl.), 1975, 49, 1265. [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]

Ermer O., 1976
Ermer O., Conformational interconversions of cis,cis-cyclooctadiene-1,5, J. Am. Chem. Soc., 1976, 98, 3964-3970. [all data]

Lebedev, Lebedev, et al., 1975
Lebedev, B.V.; Lebedev, N.K.; Kiparisova, Y.G.; Tsvetkova, L.Ya.; Rabinovich, I.B., Thermodynamics of methylenecyclobutane and 1,5-cyclooctadiene, Quatrieme Conference International de Thermodynamique Chimique, 1975, II, Thermophysique (capacites thermiques) pp. [all data]

Lebedev, Tsvetkova, et al., 1975, 2
Lebedev, B.V.; Tsvetkova, L.Ya.; Kiparisova, Y.G.; Lebedev, N.K., Thermodynamic properties of cycloocta-1,5-diene, Zhur. Fiz. Khim., 1975, 49, 2152. [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]

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]

Ott, Goates, et al., 1974
Ott, J.B.; Goates, J.R.; Reeder, J., Solid + liquid phase equilibria and solid-compound formation in hexafluorobenzene + cyclic hydrocarbons containing one or two pi-bonds, J. Chem. Thermodyn., 1974, 6, 281-5. [all data]

Cope, Stevens, et al., 1950
Cope, A.C.; Stevens, C.L.; Hochstein, F.A., Cyclic Polyolefins V. Preparation of Bromocyclooctadiens and 1,3,5-Cyclooctatriene from 1,5-Cycloctadiene, J. Am. Chem. Soc., 1950, 72, 2510-4. [all data]

Lebedev, Lebedev, et al., 1975, 2
Lebedev, B.V.; Lebedev, N.K.; Kiparisova, E.G.; Tsvetkova, L.Ya.; Rabinovich, I.B., Thermodynamics of Methlenecyclobutane and 1,5-Cyclooctadiene in II, Thermophysique, Quatrieme Confirence International de Thermodynamique Chimique, pp 20-8, 1975. [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]

Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R., Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld, Chem. Ber., 1991, 124, 2499-2521. [all data]

Turner, Mallon, et al., 1973
Turner, R.B.; Mallon, B.J.; Tichy, M.; Doering, W.v.E.; Roth, W.R.; Schroder, G., Heats of hydrogenation. X. Conjugative interaction in cyclic dienes and trienes, J. Am. Chem. Soc., 1973, 95, 8605-8610. [all data]

Taskinen and Nummelin, 1985
Taskinen, E.; Nummelin, K., Relative thermodynamic stabilities of the isomeric cyclooctadienes, Acta Chem. Scand., Ser. B, 1985, 39, 791-792. [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