1,5-Cyclooctadiene
- Formula: C8H12
- Molecular weight: 108.1809
- IUPAC Standard InChIKey: VYXHVRARDIDEHS-UHFFFAOYSA-N
- CAS Registry Number: 111-78-4
- 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: Cycloocta-1,5-diene
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 13.7 ± 0.7 | kcal/mol | Ccb | Lebedev, Tsvetkova, et al., 1975 | Heat of formtion values corrected; Author's hf298_liquid=7.6±0.7 kcal/mol; ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.049 | 50. | Dorofeeva O.V., 1986 | The value of S(298.15 K) calculated by molecular mechanics method [ Ermer O., 1976] is about 2 J/mol*K lower than that selected here.; GT |
12.76 | 100. | ||
17.08 | 150. | ||
21.94 | 200. | ||
30.096 | 273.15 | ||
33.1 ± 1.4 | 298.15 | ||
33.277 | 300. | ||
44.935 | 400. | ||
55.198 | 500. | ||
63.714 | 600. | ||
70.722 | 700. | ||
76.530 | 800. | ||
81.386 | 900. | ||
85.480 | 1000. | ||
88.948 | 1100. | ||
91.905 | 1200. | ||
94.434 | 1300. | ||
96.606 | 1400. | ||
98.480 | 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 5.8 ± 0.7 | kcal/mol | Ccb | Lebedev, Tsvetkova, et al., 1975 | Heat of formtion values corrected; Author's hf298_liquid=7.6±0.7 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1168.1 ± 0.7 | kcal/mol | Ccb | Lebedev, Tsvetkova, et al., 1975 | Heat of formtion values corrected; Author's hf298_liquid=7.6±0.7 kcal/mol; Corresponding ΔfHºliquid = 5.8 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 59.75 | cal/mol*K | N/A | Lebedev, Lebedev, et al., 1975 | DH |
S°liquid | 63.17 | cal/mol*K | N/A | Lebedev, Tsvetkova, et al., 1975, 2 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
47.54 | 298.15 | Lebedev, Lebedev, et al., 1975 | T = 6 to 320 K.; DH |
49.74 | 298.15 | Lebedev, Tsvetkova, et al., 1975, 2 | T = 10.6 to 322.7 K. Data deposited in VINITI, No. 1324-75, 15 May 1975.; DH |
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
DRB - Donald R. Burgess, Jr.
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 |
---|---|---|---|---|---|
Tboil | 422.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 422. | K | N/A | Cope and Bailey, 1948 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 203.80 | K | N/A | Ott, Goates, et al., 1974 | Uncertainty assigned by TRC = 0.06 K; TRC |
Tfus | 204. | K | N/A | Cope, Stevens, et al., 1950 | Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 201. | K | N/A | Cope, Stevens, et al., 1950 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 203.980 | K | N/A | Lebedev, Lebedev, et al., 1975, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.89 | kcal/mol | N/A | Lebedev, Tsvetkova, et al., 1975 | DRB |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.5 | 194.4 | Domalski and Hearing, 1996 | CAL |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
-0.0939 | 194.3 | crystaline, II | crystaline, I | Lebedev, Lebedev, et al., 1975 | DH |
2.349 | 203.983 | crystaline, I | liquid | Lebedev, Lebedev, et al., 1975 | DH |
-0.0911 | 194.34 | crystaline, II | crystaline, I | Lebedev, Tsvetkova, et al., 1975, 2 | Irreversible exothermic transition.; DH |
2.349 | 203.983 | crystaline, I | liquid | Lebedev, Tsvetkova, et al., 1975, 2 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
11.53 | 203.983 | crystaline, I | liquid | Lebedev, Lebedev, et al., 1975 | DH |
11.53 | 203.983 | crystaline, I | liquid | Lebedev, Tsvetkova, et al., 1975, 2 | 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 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: C8H12 + 2H2 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -55.0 ± 0.1 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
ΔrH° | -53.68 ± 0.02 | kcal/mol | Chyd | Turner, Mallon, et al., 1973 | liquid phase; solvent: Glacial acetic acid |
By formula: C8H12 = C8H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.6 ± 0.2 | kcal/mol | Eqk | Taskinen and Nummelin, 1985 | liquid phase |
By formula: C8H12 = C8H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0.7 ± 0.2 | kcal/mol | Eqk | Taskinen and Nummelin, 1985 | liquid 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 C8H12+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.9 | PE | Batich, Bischof, et al., 1973 | LLK |
9.1 ± 0.1 | EI | Davidson, Jones, et al., 1969 | RDSH |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, AND 10% IN CCl4 FOR 650-250 CM-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Petrocol DH | 923. | 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, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1164. | 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, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lebedev, Tsvetkova, et al., 1975
Lebedev, B.V.; Tsvetkova, L.Ya.; Kiparisova, E.G.; Lebedev, N.K.,
Thermodynamic properties of cyclo-octa-1,5-diene,
Russ. J. Phys. Chem. (Engl. Transl.), 1975, 49, 1265. [all data]
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]
Ermer O., 1976
Ermer O.,
Conformational interconversions of cis,cis-cyclooctadiene-1,5,
J. Am. Chem. Soc., 1976, 98, 3964-3970. [all data]
Lebedev, Lebedev, et al., 1975
Lebedev, B.V.; Lebedev, N.K.; Kiparisova, Y.G.; Tsvetkova, L.Ya.; Rabinovich, I.B.,
Thermodynamics of methylenecyclobutane and 1,5-cyclooctadiene,
Quatrieme Conference International de Thermodynamique Chimique, 1975, II, Thermophysique (capacites thermiques) pp. [all data]
Lebedev, Tsvetkova, et al., 1975, 2
Lebedev, B.V.; Tsvetkova, L.Ya.; Kiparisova, Y.G.; Lebedev, N.K.,
Thermodynamic properties of cycloocta-1,5-diene,
Zhur. Fiz. Khim., 1975, 49, 2152. [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]
Cope and Bailey, 1948
Cope, A.C.; Bailey, W.J.,
Cyclic Polyolefins II. Synthesis of Cyclooctatetraene from Chloroprene,
J. Am. Chem. Soc., 1948, 70, 2305. [all data]
Ott, Goates, et al., 1974
Ott, J.B.; Goates, J.R.; Reeder, J.,
Solid + liquid phase equilibria and solid-compound formation in hexafluorobenzene + cyclic hydrocarbons containing one or two pi-bonds,
J. Chem. Thermodyn., 1974, 6, 281-5. [all data]
Cope, Stevens, et al., 1950
Cope, A.C.; Stevens, C.L.; Hochstein, F.A.,
Cyclic Polyolefins V. Preparation of Bromocyclooctadiens and 1,3,5-Cyclooctatriene from 1,5-Cycloctadiene,
J. Am. Chem. Soc., 1950, 72, 2510-4. [all data]
Lebedev, Lebedev, et al., 1975, 2
Lebedev, B.V.; Lebedev, N.K.; Kiparisova, E.G.; Tsvetkova, L.Ya.; Rabinovich, I.B.,
Thermodynamics of Methlenecyclobutane and 1,5-Cyclooctadiene
in II, Thermophysique, Quatrieme Confirence International de Thermodynamique Chimique, pp 20-8, 1975. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R.,
Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld,
Chem. Ber., 1991, 124, 2499-2521. [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]
Taskinen and Nummelin, 1985
Taskinen, E.; Nummelin, K.,
Relative thermodynamic stabilities of the isomeric cyclooctadienes,
Acta Chem. Scand., Ser. B, 1985, 39, 791-792. [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]
Davidson, Jones, et al., 1969
Davidson, I.M.T.; Jones, M.; Kemmitt, R.D.W.,
Mass spectra and appearance potentials of some 1,5-cyclooctadiene-rhodium complexes,
J.Organometal. Chem., 1969, 17, 169. [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]
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, IR Spectrum, 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 Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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