Cyclooctene
- Formula: C8H14
- Molecular weight: 110.1968
- 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
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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: 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. |
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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Ttriple | 259.15 | K | N/A | Lebedev, Lebedev, et al., 1978 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.0 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 411. K.; AC |
9.94 | 300. | N/A | Lister, 1941 | Based on data from 273. to 333. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.433 | 259.2 | Lebedev and Smirnova, 1994 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.32 | 190.1 | Lebedev and Smirnova, 1994, 2 | CAL |
1.67 | 259.2 |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
100. | crystaline, III | crystaline, II | Lebedev, Lebedev, et al., 1978 | Glass transition.; DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.152 | 190. | crystaline, II | crystaline, I | Lebedev, Lebedev, et al., 1978 | DH |
0.4333 | 259.15 | crystaline, I | liquid | Lebedev, Lebedev, et al., 1978 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.798 | 190. | crystaline, II | crystaline, I | Lebedev, Lebedev, et al., 1978 | DH |
1.68 | 259.15 | crystaline, I | liquid | Lebedev, Lebedev, et al., 1978 | DH |
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 |
Mass spectrum (electron ionization)
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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
Spectrum
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Additional Data
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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. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-3728 |
NIST MS number | 228931 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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 | SE-30 | 130. | 922. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Capillary | SE-30 | 80. | 900. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Packed | Squalane | 100. | 905. | Bogoslovsky, Anvaer, et al., 1978 | |
Packed | Squalane | 120. | 913. | Bogoslovsky, Anvaer, et al., 1978 | |
Packed | Squalane | 27. | 875. | Bogoslovsky, Anvaer, et al., 1978 | |
Packed | Squalane | 49. | 884. | Bogoslovsky, Anvaer, et al., 1978 | |
Packed | Squalane | 67. | 892. | Bogoslovsky, Anvaer, et al., 1978 | |
Packed | Squalane | 80. | 895. | Bogoslovsky, Anvaer, et al., 1978 | |
Packed | Squalane | 86. | 900. | Bogoslovsky, Anvaer, et al., 1978 | |
Capillary | Squalane | 100. | 904. | Besson and Gäumann, 1973 | Column length: 50. m; Column diameter: 0.25 mm |
Capillary | Apiezon L | 100. | 931. | Besson and Gäumann, 1973 | Column length: 50. m; Column diameter: 0.25 mm |
Packed | Squalane | 27. | 875. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 884. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 892. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 900. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Apiezon L | 130. | 945. | Wehrli and Kováts, 1959 | Celite; Column length: 2.25 m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Petrocol DH | 888. | 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 | 910. | Buchman, Cao, et al., 1984 | He, Chromosorb AW, 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 | Petrocol DH | 889. | Supelco, 2012 | 100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 899. | Chen, 2008 | Program: not specified |
Capillary | Methyl Silicone | 945. | N/A | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 900. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 910. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 955. | Chung, Eiserich, et al., 1993 | 60. C @ 4. min, 3. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 220. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1035. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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.
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]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [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]
Lebedev and Smirnova, 1994
Lebedev, B.; Smirnova, N.,
Themodynamics of cycloalkenes, of their bulk polymerization in the presence of matathesis catalysts and of polyalkenes,
Macromol. Chem. Phys., 1994, 195, 35-63. [all data]
Lebedev and Smirnova, 1994, 2
Lebedev, B.; Smirnova, N.,
Thermodynamics of cycloalkenes, of their bulk polymerization in the presence of matathesis catalysts and of polyalkenes,
Macromol. Chem. Phys., 1994, 195, 1, 35, https://doi.org/10.1002/macp.1994.021950105
. [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]
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]
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]
Besson and Gäumann, 1973
Besson, R.; Gäumann, T.,
Indices de rétention de cycloalcanes, cycloalcènes, bicycloalkyles, cycloalkyl-cycloalcényles et bicycloalcényles en chromatographie en phase gazeuse,
Helv. Chim. Acta, 1973, 56, 3, 1159-1164, https://doi.org/10.1002/hlca.19730560339
. [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]
Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E.,
Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen,
Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745
. [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]
Supelco, 2012
Supelco, CatalogNo. 24160-U,
Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [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]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Chung, Eiserich, et al., 1993
Chung, T.Y.; Eiserich, J.P.; Shibamoto, T.,
Volatile compounds identified in headspace samples of peanut oil heated under temperatures ranging from 50 to 200 °C,
J. Agric. Food Chem., 1993, 41, 9, 1467-1470, https://doi.org/10.1021/jf00033a022
. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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 Ttriple Triple point temperature Ttrs Temperature of phase transition ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction 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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