1,3,5,7-Cyclooctatetraene
- Formula: C8H8
- Molecular weight: 104.1491
- IUPAC Standard InChIKey: KDUIUFJBNGTBMD-BONZMOEMSA-N
- CAS Registry Number: 629-20-9
- 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: [8]Annulene; Cyclooctatetraene; UN 2358
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References, Notes
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:
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 71.13 ± 0.31 | kcal/mol | N/A | Prosen, Johnson, et al., 1950 | Value computed using ΔfHliquid° value of 254.5±1.3 kj/mol from Prosen, Johnson, et al., 1950 and ΔvapH° value of 43.1±0.31 kj/mol from missing citation.; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 78.10 ± 0.35 | cal/mol*K | N/A | Scott D.W., 1949 | GT |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.564 | 50. | Dorofeeva O.V., 1986 | Selected values of Cp(T) are in close agreement with those calculated by [ Lippincott E.R., 1951], while the S(T) values are 1.5-2.0 J/mol*K larger than obtained by [ Lippincott E.R., 1951].; GT |
12.11 | 100. | ||
15.90 | 150. | ||
20.03 | 200. | ||
26.883 | 273.15 | ||
29.30 ± 0.84 | 298.15 | ||
29.484 | 300. | ||
38.678 | 400. | ||
46.465 | 500. | ||
52.811 | 600. | ||
57.995 | 700. | ||
62.292 | 800. | ||
65.894 | 900. | ||
68.939 | 1000. | ||
71.532 | 1100. | ||
73.745 | 1200. | ||
75.645 | 1300. | ||
77.280 | 1400. | ||
78.695 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References, Notes
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 | 60.82 ± 0.32 | kcal/mol | Cm | Prosen, Johnson, et al., 1950 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1084.9 ± 0.7 | kcal/mol | Ccb | Springall, White, et al., 1954 | Corresponding ΔfHºliquid = 59.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1086.50 ± 0.22 | kcal/mol | Cm | Prosen, Johnson, et al., 1950 | Corresponding ΔfHºliquid = 60.83 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 52.651 | cal/mol*K | N/A | Scott, Gross, et al., 1949 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
44.259 | 298.15 | Scott, Gross, et al., 1949 | T = 12 to 340 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas Chromatography, References, Notes
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 415.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 416. | K | N/A | Reppe, Schlichting, et al., 1948 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 265.0 | K | N/A | Cope and Bailey, 1948 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 266. | K | N/A | Reppe, Schlichting, et al., 1948 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 268.48 | K | N/A | Scott, Gross, et al., 1949, 2 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.3 ± 0.075 | kcal/mol | V | Scott, Gross, et al., 1949, 3 | ALS |
ΔvapH° | 10.3 | kcal/mol | N/A | Scott, Gross, et al., 1949 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.5 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 348. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
273. to 348. | 3.9901 | 1402.263 | -63.521 | Scott, Gross, et al., 1949 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.69460 | 268.48 | Scott, Gross, et al., 1949 | DH |
2.689 | 268.5 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.9171 | 268.48 | Scott, Gross, et al., 1949 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References, Notes
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
C8H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 382.7 ± 2.8 | kcal/mol | G+TS | Kato, Lee, et al., 1997 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 374.8 ± 2.5 | kcal/mol | IMRE | Kato, Lee, et al., 1997 | gas phase; B |
By formula: 4H2 + C8H8 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -97.96 ± 0.05 | kcal/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid; ALS |
By formula: C8H8 = C8H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -34.35 ± 0.34 | kcal/mol | Ciso | Prosen, Johnson, et al., 1947 | liquid phase; ALS |
By formula: C8H8 = c8H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 5.5 ± 0.6 | kcal/mol | Eqk | Squillacote and Bergman, 1986 | gas phase; ALS |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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: 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. | 850. | Schomburg, 1966 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 880. | Buchman, Cao, et al., 1984 | He, Chromosorb AW, 40. C @ 10. min, 10. K/min, 210. C @ 30. min; Column length: 3.05 m |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 880. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1244. | Verzera, Campisi, et al., 2005 | 60. m/0.25 mm/0.25 μm, He, 45. C @ 0.17 min, 2. K/min; Tend: 250. C |
Capillary | CP-Wax 52CB | 1244. | Verzera, Campisi, et al., 2001 | 60. m/0.25 mm/0.25 μm, He, 45. C @ 0.17 min, 2. K/min; Tend: 250. C |
Capillary | DB-Wax | 1264. | Shimoda, Peralta, et al., 1996 | 60. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 50. C; Tend: 230. C |
Packed | Carbowax 20M | 1226. | Buchman, Cao, et al., 1984 | He, Supelcoport, 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 | CP Sil 8 CB | 894. | Wang and Guo-Y. -L., 2004 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 10. K/min, 200. C @ 2. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 850. | Chen, 2008 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 880. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Packed | SE-30 | 889. | Robinson and Odell, 1971 | N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold) |
Packed | Squalane | 846. | Robinson and Odell, 1971 | N2, Embacel; Column length: 3.0 m; Program: 25C(5min) => 2C/min => 35 => 4C/min => 95C(hold) |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1244. | Editorial paper, 2005 | Program: not specified |
Capillary | DB-Wax | 1199. | Peng, Yang, et al., 1991 | Program: not specified |
Capillary | Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc. | 1226. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Prosen, Johnson, et al., 1950
Prosen, E.J.; Johnson, W.H.; Rossini, F.D.,
Heat of combustion and formation of 1,3,5,7-cyclooctatetraene and its heat of isomerization of styrene,
J. Am. Chem. Soc., 1950, 72, 626-629. [all data]
Scott D.W., 1949
Scott D.W.,
Cyclooctatetraene: low-temperature heat capacity, heat of fusion, heat of vaporization, vapor pressure, and entropy,
J. Am. Chem. Soc., 1949, 71, 1634-1636. [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]
Lippincott E.R., 1951
Lippincott E.R.,
The thermodynamic functions of cyclooctatetraene,
J. Am. Chem. Soc., 1951, 73, 3889-3891. [all data]
Springall, White, et al., 1954
Springall, H.D.; White, T.R.; Cass, R.C.,
Heats of combustion and molecular structure Part 1.- The resonance energy and structure of cyclo-octateraene,
Trans. Faraday Soc., 1954, 50, 815. [all data]
Scott, Gross, et al., 1949
Scott, D.W.; Gross, M.E.; Oliver, G.D.; Huffman, H.M.,
Cycloöctatetraene: low-temperature heat capacity, heat of fusion, heat of vaporization, vapor pressure and entropy,
J. Am. Chem. Soc., 1949, 71, 1634-1636. [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]
Reppe, Schlichting, et al., 1948
Reppe, W.; Schlichting, O.; Klager, K.; Toepel, T.,
Cyclizing Polymerization of Acetylene I. Cyclooctatetraene,
Justus Liebigs Ann. Chem., 1948, 560, 1-92. [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]
Scott, Gross, et al., 1949, 2
Scott, D.W.; Gross, M.E.; Oliver, G.D.; Huffman, H.M.,
Cyclooctatetraene: low-temperature heat capacity, heat of fusion, heat of vaporization, vapor pressure and entropy,
J. Am. Chem. Soc., 1949, 71, 1634. [all data]
Scott, Gross, et al., 1949, 3
Scott, D.W.; Gross, M.E.; Oliver, G.D.; Huffman, H.M.,
Cyclooctatetraene: Low-temperature heat capacity, heat of fusion, heat of vaporization, vapor pressure and entropy,
J. Am. Chem. Soc., 1949, 71, 1634-16. [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]
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]
Kato, Lee, et al., 1997
Kato, S.; Lee, H.S.; Gareyev, R.; Wenthold, P.G.; Lineberger, W.C.; DePuy, C.H.; Bierbaum, V.M.,
Experimental and Computational Studies of the Structures and Energetics of Cyclooctatetraene and Its Derivatives,
J. Am. Chem. Soc., 1997, 119, 33, 7863, https://doi.org/10.1021/ja971433d
. [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]
Prosen, Johnson, et al., 1947
Prosen, E.J.; Johnson, W.H.; Rossini, F.D.,
Heat of combustion and formation of 1,3,5,7-cyclooctatetraene and its heat of isomerization to styrene,
J. Am. Chem. Soc., 1947, 69, 2068-2069. [all data]
Squillacote and Bergman, 1986
Squillacote, M.E.; Bergman, A.,
Trapping of 1,3,5,7-cyclooctatetraene valence tautomers. Thermodynamic stability of bicyclo[4.2.0]octa-2,4,7-triene,
J. Org. Chem., 1986, 51, 3910-3911. [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]
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]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [all data]
Verzera, Campisi, et al., 2005
Verzera, A.; Campisi, S.; Zappalá, M.,
SUPELCO. Using SPME-GC-MS to characterize volatile components of honey as indicators of botanical origin, 2005, retrieved from http://www.sigmaaldrich.com/Brands/SupelcoHome/TheReporter.html. [all data]
Verzera, Campisi, et al., 2001
Verzera, A.; Campisi, S.; Zappalá, M.; Bonaccorsi, I.,
SPME-GC-MS analysis of honey volatile components for the characterization of different floral origin,
Am. Lab. Fairfield Conn., 2001, 33, 15, 18-21. [all data]
Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y.,
Headspace gas analysis of fish sauce,
J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u
. [all data]
Wang and Guo-Y. -L., 2004
Wang, H.-Y.; Guo-Y. -L.,
Rapid analysis of the volatile compounds in the rhizomes of Rhodiola sachalinensis and Rhodiola sacra by static headspace-gas chromatography-tandem mass spectrometry,
Anal. Letters, 2004, 37, 10, 2151-2161, https://doi.org/10.1081/AL-200026690
. [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]
Robinson and Odell, 1971
Robinson, P.G.; Odell, A.L.,
A system of standard retention indices and its uses. The characterisation of stationary phases and the prediction of retention indices,
J. Chromatogr., 1971, 57, 1-10, https://doi.org/10.1016/0021-9673(71)80001-8
. [all data]
Editorial paper, 2005
Editorial paper,
Solid Phase Microextraction (SPME) Application Guide,
The Reporter Europe (Supelco), 2005, 16, 5, 12-12. [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 Chromatography, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature 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 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 ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.