Cyclooctene, (Z)-
- Formula: C8H14
- Molecular weight: 110.1968
- IUPAC Standard InChI: InChI=1S/C8H14/c1-2-4-6-8-7-5-3-1/h1-2H,3-8H2/b2-1-
- IUPAC Standard InChIKey: URYYVOIYTNXXBN-UPHRSURJSA-N
- CAS Registry Number: 931-87-3
- 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: cis-Cyclooctene; (Z)-Cyclooctene; c-Cyclooctene
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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 | -22.7 | kJ/mol | Chyd | Doering, Roth, et al., 1989 | |
| ΔfH°gas | -28.0 ± 1.9 | kJ/mol | Chyd | Rogers, Von Voithenberg, et al., 1978 |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 418.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Tboil | 418. | K | N/A | Treboganov, Mitsner, et al., 1965 | Uncertainty assigned by TRC = 1. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 258.2 | K | N/A | Cope, Pike, et al., 1953 | Uncertainty assigned by TRC = 3. K; TRC |
| Tfus | 261. | K | N/A | Ziegler and Wilms, 1950 | Uncertainty assigned by TRC = 3. K; TRC |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 41.57 | 300. | V | Lister, 1941 | Heat of bromination at 300 K; ALS |
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
+
=
By formula: H2 + C8H14 = C8H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -102. | kJ/mol | Chyd | Doering, Roth, et al., 1989 | liquid phase |
| ΔrH° | -103. ± 0.8 | kJ/mol | Chyd | Roth and Lennartz, 1980 | liquid phase; solvent: Cyclohexane |
| ΔrH° | -96.40 ± 0.71 | kJ/mol | Chyd | Rogers, Von Voithenberg, et al., 1978 | liquid phase; solvent: Hexane |
| ΔrH° | -96.1 ± 0.4 | kJ/mol | Chyd | Turner and Meador, 1957 | liquid phase; solvent: Acetic acid |
| ΔrH° | -97.40 ± 0.63 | kJ/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -98.4 ± 0.2 kJ/mol; At 355 K |
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 by: Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference |
|---|---|---|
| 8.82 | PE | Bischof and Heilbronner, 1970 |
References
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Cope, Pike, et al., 1953
Cope, A.C.; Pike, R.A.; Spencer, C.F.,
Cyclic Polyolefins XVII. cis- and trans-Cyclooctene from N,N-Dimethylcyclooctylamine,
J. Am. Chem. Soc., 1953, 75, 3212. [all data]
Ziegler and Wilms, 1950
Ziegler, K.; Wilms, H.,
Polymembered Ring Systems XIII. Eight-membered Cycloolefin Rings,
Justus Liebigs Ann. Chem., 1950, 567, 1-43. [all data]
Lister, 1941
Lister, M.W.,
Heats of organic reactions. X. Heats of bromination of cyclic olefins,
J. Am. Chem. Soc., 1941, 63, 143-149. [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]
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Bischof and Heilbronner, 1970
Bischof, P.; Heilbronner, E.,
Photoelektron-Spektren von Cycloalkenen und Cycloalkadienen,
Helv. Chim. Acta, 1970, 53, 1677. [all data]
Notes
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- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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