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Cyclooctane

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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
Deltafgas-126.1 ± 1.6kJ/molN/ASpitzer and Huffman, 1947Value computed using «DELTA»fHliquid° value of -169.4±1.6 kj/mol from Spitzer and Huffman, 1947 and «DELTA»vapH° value of 43.35±0.21 kj/mol from missing citation.; DRB
Quantity Value Units Method Reference Comment
gas366.8 ± 1.3J/mol*KN/AFinke H.L., 1956GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
38.6250.Dorofeeva O.V., 1986S(T) values calculated by [ Stull D.R., 1969] are in good agreement with those selected here; however, the discrepancy in Cp(298.15 K) amounts to 6.2 J/mol*K. S(T) values calculated by molecular mechanics method [ Chang S., 1970] are about 13 J/mol*K less than recommended ones; discrepancies in Cp(T) values amount to 1-2 J/mol*K.; GT
64.77100.
83.16150.
99.99200.
133.07273.15
146.2 ± 5.0298.15
147.19300.
202.16400.
253.07500.
296.64600.
333.38700.
364.46800.
390.90900.
413.471000.
432.791100.
449.361200.
463.611300.
475.901400.
486.531500.

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
Deltafliquid-169.4 ± 1.6kJ/molCcbSpitzer and Huffman, 1947Reanalyzed by Cox and Pilcher, 1970, Original value = -169.9 ± 2.5 kJ/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-5265.7 ± 0.9kJ/molCcbKaarsemaker and Coops, 1952Corresponding «DELTA»fliquid = -169.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-5265.3 ± 1.6kJ/molCcbSpitzer and Huffman, 1947Reanalyzed by Cox and Pilcher, 1970, Original value = -5264.9 ± 1.6 kJ/mol; Corresponding «DELTA»fliquid = -169.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid262.00J/mol*KN/AFinke, Scott, et al., 1956DH
Quantity Value Units Method Reference Comment
Deltacsolid-5252.6kJ/molCcbRuzieka and Schlapfer, 1933Heat of combustion corrected for pressure; Corresponding «DELTA»fsolid = -182. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
215.78298.15Shiohama, Ogawa, et al., 1988DH
215.53298.15Tanaka, 1985DH
215.461298.15Fortier, D'Arcy, et al., 1979DH
214.53298.15Wilhelm, Faradjzadeh, et al., 1979DH
214.24298.15Jolicoeur, Boileau, et al., 1975DH
215.48298.15Finke, Scott, et al., 1956T = 12 to 330 K.; DH

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

Hydrogen + Cyclooctene, (Z)- = Cyclooctane

By formula: H2 + C8H14 = C8H16

Quantity Value Units Method Reference Comment
Deltar-102.kJ/molChydDoering, Roth, et al., 1989liquid phase
Deltar-103. ± 0.8kJ/molChydRoth and Lennartz, 1980liquid phase; solvent: Cyclohexane
Deltar-96.40 ± 0.71kJ/molChydRogers, Von Voithenberg, et al., 1978liquid phase; solvent: Hexane
Deltar-96.1 ± 0.4kJ/molChydTurner and Meador, 1957liquid phase; solvent: Acetic acid
Deltar-97.40 ± 0.63kJ/molChydConn, Kistiakowsky, et al., 1939gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -98.4 ± 0.2 kJ/mol; At 355 K

Hydrogen + trans-Cyclooctene = Cyclooctane

By formula: H2 + C8H14 = C8H16

Quantity Value Units Method Reference Comment
Deltar-144. ± 0.4kJ/molChydRoth, Adamczak, et al., 1991liquid phase; see Doering, Roth, et al., 1989
Deltar-144.0 ± 1.8kJ/molChydRogers, Von Voithenberg, et al., 1978liquid phase; solvent: Hexane
Deltar-134.9 ± 0.88kJ/molChydTurner and Meador, 1957liquid phase; solvent: Acetic acid

3Hydrogen + 1,3,5-Cyclooctatriene = Cyclooctane

By formula: 3H2 + C8H10 = C8H16

Quantity Value Units Method Reference Comment
Deltar-319.6 ± 1.8kJ/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Acetic acid
Deltar-302.8 ± 1.1kJ/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid

2Hydrogen + Cyclooctyne = Cyclooctane

By formula: 2H2 + C8H12 = C8H16

Quantity Value Units Method Reference Comment
Deltar-291. ± 0.8kJ/molChydRoth, Hopf, et al., 1994liquid phase; solvent: Isooctane
Deltar-289.kJ/molChydTurner, Jarrett, et al., 1973liquid phase; solvent: Acetic acid

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

2Hydrogen + 1,3-Cyclooctadiene, (Z,Z)- = Cyclooctane

By formula: 2H2 + C8H12 = C8H16

Quantity Value Units Method Reference Comment
Deltar-208.kJ/molChydRoth, Adamczak, et al., 1991liquid phase
Deltar-204.8 ± 0.3kJ/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Glacial acetic acid

1,4-Cyclooctadiene + 2Hydrogen = Cyclooctane

By formula: C8H12 + 2H2 = C8H16

Quantity Value Units Method Reference Comment
Deltar-217.9 ± 1.2kJ/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Glacial acetic acid

3Hydrogen + 1,3,6-Cyclooctatriene = Cyclooctane

By formula: 3H2 + C8H10 = C8H16

Quantity Value Units Method Reference Comment
Deltar-334.3 ± 0.71kJ/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Glacial acetic acid

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

4Hydrogen + 1,5-Cyclooctadiyne = Cyclooctane

By formula: 4H2 + C8H8 = C8H16

Quantity Value Units Method Reference Comment
Deltar640. ± 1.kJ/molChydRoth, Hopf, et al., 1994liquid phase; solvent: Isooctane

Hydrogen + Cyclooctene = Cyclooctane

By formula: H2 + C8H14 = C8H16

Quantity Value Units Method Reference Comment
Deltar-94. ± 1.kJ/molChydRogers and McLafferty, 1971liquid phase; solvent: Acetic acid

2Hydrogen + 1,5-Cyclooctadiene, (E,E)- = Cyclooctane

By formula: 2H2 + C8H12 = C8H16

Quantity Value Units Method Reference Comment
Deltar-320. ± 0.4kJ/molChydRoth, Adamczak, et al., 1991liquid phase

2Hydrogen + (Z,E)-1,3-Cyclooctadiene = Cyclooctane

By formula: 2H2 + C8H12 = C8H16

Quantity Value Units Method Reference Comment
Deltar-271. ± 0.4kJ/molChydRoth, Adamczak, et al., 1991liquid phase

2Hydrogen + 1,5-Cyclooctadiene, (E,Z)- = Cyclooctane

By formula: 2H2 + C8H12 = C8H16

Quantity Value Units Method Reference Comment
Deltar-282. ± 0.4kJ/molChydRoth, Adamczak, et al., 1991liquid phase

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Spitzer and Huffman, 1947
Spitzer, R.; Huffman, H.M., The heats of combustion of cyclopentane, cyclohexane, cycloheptane and cyclooctane, J. Am. Chem. Soc., 1947, 69, 211-213. [all data]

Finke H.L., 1956
Finke H.L., Cycloheptane, cyclooctane, and 1,3,5-cycloheptatriene. Low-temperature thermal properties, vapor pressure, and derived chemical thermodynamic properties, J. Am. Chem. Soc., 1956, 78, 5469-5476. [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]

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

Chang S., 1970
Chang S., The heats of combustion and strain energies of bicyclo[n.m.0]alkanes, J. Am. Chem. Soc., 1970, 92, 3109-3118. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Kaarsemaker and Coops, 1952
Kaarsemaker, S.; Coops, J., Thermal quantities of some cycloparaffins. Part III. Results of measurements, Rec. Trav. Chim. Pays/Bas, 1952, 71, 261. [all data]

Finke, Scott, et al., 1956
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G., Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties, J. Am. Chem. Soc., 1956, 78, 5469-5476. [all data]

Ruzieka and Schlapfer, 1933
Ruzieka, L.; Schlapfer, P., Zur kenntnis des kohlenstoffringes XXII. Uber die verbrennungswarme bei hochgliedrigen ringverbindungen, Helv. Chim. Acta, 1933, 16, 162-169. [all data]

Shiohama, Ogawa, et al., 1988
Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I., Excess thermodynamic properties of (cis-decalin or trans-decalin + cyclohexane or methylcyclohexane or cyclooctane) at 298.15 K, J. Chem. Thermodynam., 1988, 20, 1307-1314. [all data]

Tanaka, 1985
Tanaka, R., Excess heat capacities for mixtures of benzene with cyclopentane, methylcyclohexane, and cyclooctane at 298.15 K, J. Chem. Eng. Data, 1985, 30, 267-269. [all data]

Fortier, D'Arcy, et al., 1979
Fortier, J.-L.; D'Arcy, P.J.; Benson, G.C., Heat capacities of binary cycloalkane mixtures at 298.15 K, Thermochim. Acta, 1979, 28, 37-43. [all data]

Wilhelm, Faradjzadeh, et al., 1979
Wilhelm, E.; Faradjzadeh, A.; Grolier, J.-P.E., Molar excess heat capacities and excess volumes of 1,2-dichloroethane + cyclooctane, + mesitylene, and + tetrachloromethane, J. Chem. Thermodynam., 1979, 11, 979-984. [all data]

Jolicoeur, Boileau, et al., 1975
Jolicoeur, C.; Boileau, J.; Bazinet, S.; Picker, P., Thermodynamic properties of aqueous organic solutes in relation to their structure. Part II. Apparent molal volumes and heat capacities of c-alkylamine hydrobromides in water, Can. J. Chem., 1975, 53, 716-722. [all data]

Doering, Roth, et al., 1989
Doering, W.E.; Roth, W.R.; Bauer, F.; Breuckmann, R.; Ebbrecht, T.; Herbold, M.; Schmidt, R.; Lennartz, H-W.; Lenoir, D.; Boese, R., Rotational barriers of strained olefines, Chem. Ber., 1989, 122, 1263-1266. [all data]

Roth and Lennartz, 1980
Roth, W.R.; Lennartz, H.W., Heats of hydrogenation. I. Determination of heats of hydrogenation with an isothermal titration calorimeter, Chem. Ber., 1980, 113, 1806-1817. [all data]

Rogers, Von Voithenberg, et al., 1978
Rogers, D.W.; Von Voithenberg, H.; Allinger, N.L., Heats of hydrogenation of the cis and trans isomers of cyclooctene, J. Org. Chem., 1978, 43, 360-361. [all data]

Turner and Meador, 1957
Turner, R.B.; Meador, W.R., Heats of hydrogenation. IV. Hydrogenation of some cis- and trans-cycloolefins, J. Am. Chem. Soc., 1957, 79, 4133-4136. [all data]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [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]

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]

Roth, Hopf, et al., 1994
Roth, W.R.; Hopf, H.; Horn, C., Propargyl-Stabilisierungsenergie, Chem. Ber., 1994, 127, 1781-1795. [all data]

Turner, Jarrett, et al., 1973
Turner, R.B.; Jarrett, A.D.; Goebel, P.; Mallon, B.J., Heats of hydrogenation. 9. Cyclic acetylenes and some miscellaneous olefins, J. Am. Chem. Soc., 1973, 95, 790-792. [all data]

Rogers and McLafferty, 1971
Rogers, D.W.; McLafferty, F.J., A new hydrogen calorimeter. Heats of hydrogenation of allyl and vinyl unsaturation adjacent to a ring, Tetrahedron, 1971, 27, 3765-3775. [all data]


Notes

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