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1,5-Cyclooctadiene

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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:
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
Deltafgas57. ± 3.kJ/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 (J/mol*K) Temperature (K) Reference Comment
37.8650.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
53.37100.
71.48150.
91.78200.
125.92273.15
138.3 ± 6.0298.15
139.23300.
188.01400.
230.95500.
266.58600.
295.90700.
320.20800.
340.52900.
357.651000.
372.161100.
384.531200.
395.111300.
404.201400.
412.041500.

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
Deltafliquid24. ± 3.kJ/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
Deltacliquid-4887. ± 3.kJ/molCcbLebedev, Tsvetkova, et al., 1975Heat of formtion values corrected; Author's hf298_liquid=7.6±0.7 kcal/mol; Corresponding «DELTA»fliquid = 24. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid250.0J/mol*KN/ALebedev, Lebedev, et al., 1975DH
liquid264.3J/mol*KN/ALebedev, Tsvetkova, et al., 1975, 2DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
198.9298.15Lebedev, Lebedev, et al., 1975T = 6 to 320 K.; DH
208.1298.15Lebedev, 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

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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
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
Deltavap33.0kJ/molN/ALebedev, Tsvetkova, et al., 1975DRB

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
48.2194.4Domalski and Hearing, 1996CAL

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
-0.393194.3crystaline, IIcrystaline, ILebedev, Lebedev, et al., 1975DH
9.828203.983crystaline, IliquidLebedev, Lebedev, et al., 1975DH
-0.381194.34crystaline, IIcrystaline, ILebedev, Tsvetkova, et al., 1975, 2Irreversible exothermic transition.; DH
9.828203.983crystaline, IliquidLebedev, Tsvetkova, et al., 1975, 2DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
48.24203.983crystaline, IliquidLebedev, Lebedev, et al., 1975DH
48.24203.983crystaline, 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

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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: 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
Deltar-230. ± 0.4kJ/molChydRoth, Adamczak, et al., 1991liquid phase
Deltar-224.6 ± 0.08kJ/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
Deltar-19.4 ± 0.9kJ/molEqkTaskinen and Nummelin, 1985liquid phase

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

By formula: C8H12 = C8H12

Quantity Value Units Method Reference Comment
Deltar-2.8 ± 0.8kJ/molEqkTaskinen and Nummelin, 1985liquid phase

Gas phase ion energetics 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C8H12+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.9PEBatich, Bischof, et al., 1973LLK
9.1 ± 0.1EIDavidson, Jones, et al., 1969RDSH

IR Spectrum

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

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Gas Chromatography

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), NIST Free Links, 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

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPetrocol DH923.Supelco, 2012100. m/0.25 mm/0.50 «mu»m, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1164.Peng, Yang, et al., 1991Program: not specified

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), Gas Chromatography, NIST Free Links, 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]

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]

Davidson, Jones, et al., 1969
Davidson, I.M.T.; Jones, M.; Kemmitt, R.D.W., Mass spectra and appearance potentials of some 1,5-cyclooctadiene-rhodium complexes, J.Organometal. Chem., 1969, 17, 169. [all data]

Supelco, 2012
Supelco, CatalogNo. 24160-U, Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [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 phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References