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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Condensed phase thermochemistry data
Go To: Top, Mass spectrum (electron ionization), Gas Chromatography, 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | 57.7 ± 1.4 | kJ/mol | Ccb | Kozina, Timofeeva, et al., 1976 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -4920.8 ± 1.3 | kJ/mol | Ccb | Kozina, Timofeeva, et al., 1976 | Corresponding ΔfHºliquid = 57.70 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -4880.6 | kJ/mol | Ccr | Rauh, Geyer, et al., 1973 | Corresponding ΔfHºliquid = 18. kJ/mol (simple calculation by NIST; no Washburn corrections) |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Gas Chromatography, 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
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Additional Data
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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. |
|---|---|
| NIST MS number | 1406 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | OV-1 | 160. | 959. | Zhang, Chen, et al., 1997 | 25. m/0.2 mm/0.33 μm, N2 |
| Capillary | OV-1 | 100. | 931.1 | Engewald, Billing, et al., 1987 | Column length: 50. m; Column diameter: 0.3 mm |
| Capillary | SE-30 | 130. | 946. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
| Capillary | SE-30 | 80. | 926. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
| Packed | Squalane | 120. | 923. | Bogoslovsky, Anvaer, et al., 1978 | |
| Packed | Squalane | 70. | 915. | Bogoslovsky, Anvaer, et al., 1978 | |
| Capillary | Squalane | 42.5 | 907. | Engewald, Epsch, et al., 1974 | N2; Column length: 100. m; Column diameter: 0.23 mm |
| Capillary | Squalane | 80. | 915. | Engewald, Epsch, et al., 1974 | N2; Column length: 100. m; Column diameter: 0.23 mm |
| Packed | Squalane | 49. | 903. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 67. | 911. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Packed | Squalane | 86. | 918. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
| Capillary | Squalane | 100. | 923. | Schomburg, 1967 | Ar; Column length: 100. m |
| Capillary | Squalane | 70. | 915. | Schomburg, 1966 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Petrocol DH | 917. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
| Packed | SE-30 | 949. | Buchman, Cao, et al., 1984 | He, Chromosorb AW, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | Carbowax 20M | 1188. | Buchman, Cao, et al., 1984 | He, Supelcoport, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-1 | 928. | Orav, Kailas, et al., 1999 | 2. K/min; Tstart: 50. C; Tend: 160. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Squalane | 926. | Chen, 2008 | Program: not specified |
| Capillary | OV-101 | 871. | Zenkevich and Malamakhov, 1987 | He; Column length: 50. m; Column diameter: 0.24 mm; Program: not specified |
| Packed | SE-30 | 948. | Robinson and Odell, 1971 | N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold) |
| Packed | Squalane | 917. | Robinson and Odell, 1971 | N2, Embacel; Column length: 3.0 m; Program: 25C(5min) => 2C/min => 35 => 4C/min => 95C(hold) |
| Packed | Squalane | 917. | Robinson and Odell, 1971, 2 | Embacel; Column length: 3.0 m; Program: 25C(5min) => 2C/min(5min) => 4C/min(15min) => (hold at 95C) |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 144.4 | Donnelly, Abdel-Hamid, et al., 1993 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 3. min, 8. K/min, 285. C @ 29.5 min |
References
Go To: Top, Condensed phase thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, 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]
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]
Zhang, Chen, et al., 1997
Zhang, M.; Chen, B.; Shen, S.; Chen, S.,
Compositional studies of high-temperature coal tar by g.c.-FT-i.r. analysis of middle oil fractions,
Fuel, 1997, 76, 5, 415-423, https://doi.org/10.1016/S0016-2361(97)85518-4
. [all data]
Engewald, Billing, et al., 1987
Engewald, W.; Billing, U.; Welsch, T.; Haufe, G.,
Structure-retention correlations of hydrocarbons in gas-liquid and gas-solid chromatography. Cycloalkenes and cycloalkadienes,
Chromatographia, 1987, 23, 8, 590-594, https://doi.org/10.1007/BF02324870
. [all data]
Bredael, 1982
Bredael, P.,
Retention indices of hydrocarbons on SE-30,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610
. [all data]
Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S.,
Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]
Engewald, Epsch, et al., 1974
Engewald, W.; Epsch, K.; Graefe, J.; Welsch, Th.,
Molekülstruktur und retentionsverhalten. II. Retentionsverhalten cycloaliphatischer kohlenwasser-stoffe bei der gas-adsorptions- und gas-verteilungschromatographie,
J. Chromatogr., 1974, 91, 623-631, https://doi.org/10.1016/S0021-9673(01)97943-9
. [all data]
Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E.,
Variation of the retention index with temperature on squalane substrates,
J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203
. [all data]
Schomburg, 1967
Schomburg, G.,
Struktur und Retentionsverhalten von Offenkettigen und Cyclischen Kohlenwasserstoffen und Deren Einfacher Substitutionsprodukte,
Anal. Chim. Acta., 1967, 38, 45-64, https://doi.org/10.1016/S0003-2670(01)80560-2
. [all data]
Schomburg, 1966
Schomburg, G.,
Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe,
J. Chromatogr., 1966, 23, 18-41, https://doi.org/10.1016/S0021-9673(01)98653-4
. [all data]
White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S.,
Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane,
J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211
. [all data]
Buchman, Cao, et al., 1984
Buchman, O.; Cao, G.-Y.; Peng, C.T.,
Structure assignment by retention index in gas-liquid radiochromatography of substituted cyclohexenes,
J. Chromatogr., 1984, 312, 75-90, https://doi.org/10.1016/S0021-9673(01)92765-7
. [all data]
Orav, Kailas, et al., 1999
Orav, A.; Kailas, T.; Muurisepp, M.; Kann, J.,
Composition of the oil from waste tires. 2. Fraction boiling at 160-180 0C,
Proc. Estonian Acad. Sci. Chem., 1999, 48, 3, 136-140. [all data]
Chen, 2008
Chen, H.-F.,
Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression,
Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003
. [all data]
Zenkevich and Malamakhov, 1987
Zenkevich, I.G.; Malamakhov, A.C.,
Evaluation of Molecular Weights of Organic Compounds based on Retention Parameters at Chromato-Spectral Analysys. Additional Criterion of Molecular Ions' Identification,
Vestn. St. Petersb. Univ. Ser. 4: Fiz. Khim, 1987, 2, 101-106. [all data]
Robinson and Odell, 1971
Robinson, P.G.; Odell, A.L.,
A system of standard retention indices and its uses. The characterisation of stationary phases and the prediction of retention indices,
J. Chromatogr., 1971, 57, 1-10, https://doi.org/10.1016/0021-9673(71)80001-8
. [all data]
Robinson and Odell, 1971, 2
Robinson, P.G.; Odell, A.L.,
Comparison of isothermal and non-linear temperature programmed gas chromatography. The temperature dependence of the retention indices of a number of hydrocarbons on squalane and SE-30,
J. Chromatogr., 1971, 57, 11-17, https://doi.org/10.1016/0021-9673(71)80002-X
. [all data]
Donnelly, Abdel-Hamid, et al., 1993
Donnelly, J.R.; Abdel-Hamid, M.S.; Jeter, J.L.; Gurka, D.F.,
Application of gas chromatographic retention properties to the identification of environmental contaminants,
J. Chromatogr., 1993, 642, 1-2, 409-415, https://doi.org/10.1016/0021-9673(93)80106-I
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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