1,5-Cyclooctadiene
- Formula: C8H12
- Molecular weight: 108.1809
- IUPAC Standard InChI: InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2
- 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
View 3d structure (requires JavaScript / HTML 5) - 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 |
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
+ 2
=
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 |
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
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
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
| 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- 886 |
| NIST MS number | 228933 |
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
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, Reaction thermochemistry data, IR Spectrum, 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.
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]
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]
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, Reaction thermochemistry data, IR Spectrum, 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 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 ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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