1,5-Cyclooctadiene, (Z,Z)-
- Formula: C8H12
- Molecular weight: 108.1809
- IUPAC Standard InChI: InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7-
- IUPAC Standard InChIKey: VYXHVRARDIDEHS-QGTKBVGQSA-N
- CAS Registry Number: 1552-12-1
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Stereoisomers:
- Other names: (Z,Z)-1,5-Cyclooctadiene; cis,cis-1,5-Cyclooctadiene; COD; cis,cis-Cycloocta-1,5-diene; 1,5-Cyclooctadiene; (Z,Z)-cycloocta-1,5-diene
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 101.0 ± 1.4 | kJ/mol | Ccb | Kozina, Timofeeva, et al., 1976 |
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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 420. | K | N/A | Treboganov, Mitsner, et al., 1965 | Uncertainty assigned by TRC = 2. K; TRC |
| Tboil | 421. | K | N/A | Zakharkin and Zhigareva, 1963 | Uncertainty assigned by TRC = 2. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 203. | K | N/A | Ziegler and Wilms, 1948 | Uncertainty assigned by TRC = 5. K; stereochemistry not certain; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 43.39 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
| ΔvapH° | 43.4 ± 0.1 | kJ/mol | C | Varushchenko, Pashchenko, et al., 1996 | AC |
| ΔvapH° | 43.3 | kJ/mol | N/A | Kozina, Timofeeva, et al., 1976 | DRB |
| ΔvapH° | 41.0 | kJ/mol | V | Rauh, Geyer, et al., 1973 | ALS |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Kozina, Timofeeva, et al., 1976
Kozina, M.P.; Timofeeva, L.P.; Gal'chenko, G.L.; Gvozdeva, E.A.; Cherednichenko, V.M.,
The determination of the enthalphy of combustion of cis, cis-cyclooctadiene-1,5,
Termodin. Org. Soedin., 1976, 9-11. [all data]
Treboganov, Mitsner, et al., 1965
Treboganov, A.D.; Mitsner, B.I.; Zinkevich, E.P.; Kraevskii, A.A.; Preobrazhenskii, N.A.,
Macrocyclic compounds. I. Synthesis of cyclooctane and cyclododecane,
Zh. Organ. Khim., 1965, 1, 1583-6. [all data]
Zakharkin and Zhigareva, 1963
Zakharkin, L.I.; Zhigareva, G.G.,
Dimerization of butadiene to cis-cis-1,5-cyclooctadiene catalyzed by pi-complex compounds of nickel,
Izv. Akad. Nauk SSSR, 1963, Otd. Khim. Nauk 386 1963 1963. [all data]
Ziegler and Wilms, 1948
Ziegler, K.; Wilms, H.,
Stereoisomerism of Eight-membered Cycloolefin Rings,
Naturwissenschaften, 1948, 35, 157-8. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Varushchenko, Pashchenko, et al., 1996
Varushchenko, R.M.; Pashchenko, L.L.; Druzhinina, A.I.,
Enthalpies of vaporization of some mono- and polycyclic hydrocarbons,
Zh. Fiz. Khim., 1996, 70, 2, 228. [all data]
Rauh, Geyer, et al., 1973
Rauh, H.J.; Geyer, W.; Schmidt, H.; Geiseler, G.,
Bildungsenthalpien und mesomerieenergien von π-bindungssystemen,
Z. Phys. Chem. (Leipzig), 1973, 253, 43-48. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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