1,3,5-Cyclooctatriene
- Formula: C8H10
- Molecular weight: 106.1650
- IUPAC Standard InChIKey: ICPMUWPXCAVOOQ-XCADPSHZSA-N
- CAS Registry Number: 1871-52-9
- 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. - Other names: Cycloocta-1,3,5-triene
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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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 418.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 189.9 | K | N/A | Cope and Hochstein, 1950 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 183.2 | K | N/A | Cope and Hochstein, 1950 | Uncertainty assigned by TRC = 4. K; TRC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
349.2 | 0.12 | Weast and Grasselli, 1989 | BS |
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: 3H2 + C8H10 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -319.6 ± 1.8 | kJ/mol | Chyd | Turner, Mallon, et al., 1973 | liquid phase; solvent: Acetic acid |
ΔrH° | -302.8 ± 1.1 | kJ/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid |
By formula: C8H10 = C8H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0.58 ± 0.07 | kJ/mol | Eqk | Greathead and Orchard, 1983 | gas phase |
By formula: C8H10 = C8H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -13.6 ± 0.2 | kJ/mol | Eqk | Greathead and Orchard, 1983 | gas phase |
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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C8H10+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.9 | PE | Batich, Bischof, et al., 1973 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C8H9+ | 10.8 | H | EI | Grutzmacher, 1970 | RDSH |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Source | Cope and Ester, 1950 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 9793 |
Instrument | Beckman DU |
Melting point | - 62 |
Boiling point | 145.5 |
Gas Chromatography
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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: 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 | Squalane | 70. | 905. | Schomburg, 1966 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 890. | Gómez, Ledbetter, et al., 1993 | He, 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 250. C |
References
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, UV/Visible spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Cope and Hochstein, 1950
Cope, A.C.; Hochstein, F.A.,
Cyclic Polyolefins VI. Preparation of Cyclooctatrienes from \ Cyclooctatetraene,
J. Am. Chem. Soc., 1950, 72, 2515-20. [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]
Greathead and Orchard, 1983
Greathead, J.M.; Orchard, S.W.,
Kinetic and equilibrium study of gas-phase interconversions of 1,3,6-cyclooctatriene, 1,3,5-cyclooctatriene and bicyclo[4.2.0]octa-2,4-diene,
Int. J. Chem. Kinet., 1983, 15, 1069-1080. [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]
Grutzmacher, 1970
Grutzmacher, H.-F.,
Zum Mechanismus massenspektrometrischer Fragmentierungsreaktionen-IV: zur Bildung von Phenonium-Ionen bei der Elektronenstoss-Fragmentierung von -Phenylathylbromiden,
Org. Mass Spectrom., 1970, 3, 131. [all data]
Cope and Ester, 1950
Cope, A.C.; Ester, L.L.,
J. Am. Chem. Soc., 1950, 72, 1123. [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]
Gómez, Ledbetter, et al., 1993
Gómez, E.; Ledbetter, C.A.; Hartsell, P.L.,
Volatile compounds in apricot, plum, and their interspecific hybrids,
J. Agric. Food Chem., 1993, 41, 10, 1669-1676, https://doi.org/10.1021/jf00034a029
. [all data]
Notes
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- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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