Cyclooctene
- 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
- IUPAC Standard InChIKey: URYYVOIYTNXXBN-UHFFFAOYSA-N
- CAS Registry Number: 931-88-4
- 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)-Cyclooctene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 8.728 | 50. | Dorofeeva O.V., 1986 | |
| 12.50 | 100. | ||
| 17.28 | 150. | ||
| 22.39 | 200. | ||
| 30.987 | 273.15 | ||
| 34.2 ± 1.4 | 298.15 | ||
| 34.393 | 300. | ||
| 47.067 | 400. | ||
| 58.329 | 500. | ||
| 67.732 | 600. | ||
| 75.533 | 700. | ||
| 82.063 | 800. | ||
| 87.581 | 900. | ||
| 92.275 | 1000. | ||
| 96.281 | 1100. | ||
| 99.716 | 1200. | ||
| 102.66 | 1300. | ||
| 105.21 | 1400. | ||
| 107.41 | 1500. |
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 by: Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| S°liquid | 60.83 | cal/mol*K | N/A | Lebedev, Lebedev, et al., 1978 |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 49.67 | 298.15 | Lebedev, Lebedev, et al., 1978 | T = 8 to 330 K. |
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 as indicated in comments:
B - John E. Bartmess
ALS - 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: C8H13- + H+ = C8H14
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 386.5 ± 5.1 | kcal/mol | G+TS | Lee and Squires, 1986 | gas phase; Between H2O, MeOH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 379.0 ± 5.0 | kcal/mol | IMRB | Lee and Squires, 1986 | gas phase; Between H2O, MeOH; B |
+
=
By formula: H2 + C8H14 = C8H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -22.4 ± 0.3 | kcal/mol | Chyd | Rogers and McLafferty, 1971 | liquid phase; solvent: Acetic acid; ALS |
+
=
By formula: Br2 + C8H14 = C8H14Br2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -29.310 | kcal/mol | Cm | Lister, 1941 | gas phase; Heat of bromination at 300 K; ALS |
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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.8 | PE | Batich, Bischof, et al., 1973 | LLK |
| 9.02 | PE | Hentrich, Gunkel, et al., 1974 | Vertical value; LLK |
De-protonation reactions
+
=
By formula: C8H13- + H+ = C8H14
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 386.5 ± 5.1 | kcal/mol | G+TS | Lee and Squires, 1986 | gas phase; Between H2O, MeOH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 379.0 ± 5.0 | kcal/mol | IMRB | Lee and Squires, 1986 | gas phase; Between H2O, MeOH; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Lebedev, Lebedev, et al., 1978
Lebedev, B.V.; Lebedev, N.K.; Lityagov, Y.Va.; Mukhina, N.N.,
Thermodynamic characteristics of cyclooctene and polyoctenylene and process for the polymerization of cyclooctene in the range 8-330 K,
Termodin. Org. Soedin., 1978, (7), 23-37. [all data]
Lee and Squires, 1986
Lee, R.E.; Squires, R.R.,
Anionic homoaromaticity: A gas phase experimental study,
J. Am. Chem. Soc., 1986, 105, 5078. [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]
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]
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]
Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M.,
Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen,
J. Mol. Struct., 1974, 21, 231. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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