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1,3-Cyclohexadiene

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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
Deltafgas25.00 ± 0.15kcal/molCcrSteele, Chirico, et al., 1989ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
8.18450.Dorofeeva O.V., 1986Recommended entropy values at 298.15 and 1000 K are less than those obtained by force-field calculation [ Lenz T.G., 1989] by 6.6 and 5.0 J/mol*K, respectively. Discrepancies between Cp(T) values amount to about 3 J/mol*K.; GT
9.747100.
12.01150.
15.00200.
20.47273.15
22.51 ± 0.60298.15
22.66300.
30.724400.
37.761500.
43.556600.
48.313700.
52.271800.
55.600900.
58.4251000.
60.8341100.
62.8971200.
64.6701300.
66.2001400.
67.5241500.

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
Deltafliquid17.07 ± 0.15kcal/molCcrSteele, Chirico, et al., 1989ALS
Quantity Value Units Method Reference Comment
Deltacliquid-854.63 ± 0.13kcal/molCcrSteele, Chirico, et al., 1989Corresponding «DELTA»fliquid = 17.07 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid47.151cal/mol*KN/AGeipel and Wolf, 1976DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
33.77298.15Steele, Chirico, et al., 1989DH
34.551298.15Geipel and Wolf, 1976T = 10 to 300 K.; 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

C6H7- + Hydrogen cation = 1,3-Cyclohexadiene

By formula: C6H7- + H+ = C6H8

Quantity Value Units Method Reference Comment
Deltar373.2 ± 4.1kcal/molG+TSLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar365.8 ± 4.0kcal/molIMRBLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; B

2Hydrogen + 1,3-Cyclohexadiene = Cyclohexane

By formula: 2H2 + C6H8 = C6H12

Quantity Value Units Method Reference Comment
Deltar-53.64 ± 0.29kcal/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Glacial acetic acid; ALS
Deltar-54.88 ± 0.10kcal/molChydKistiakowsky, Ruhoff, et al., 1936gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -55.4 ± 0.1 kcal/mol; At 355 °K; ALS

Bicyclo[2.2.2]oct-2-ene = 1,3-Cyclohexadiene + Ethylene

By formula: C8H12 = C6H8 + C2H4

Quantity Value Units Method Reference Comment
Deltar32.4kcal/molKinHuybrechts, Rigaux, et al., 1980gas phase; Diels-Alder addition at 560°K, see Van Mele, Boon, et al., 1986; ALS

2,3-Diazabicyclo[2.2.2]octa-2,5-diene N-oxide = Nitrous oxide + 1,3-Cyclohexadiene

By formula: C6H8N2O = N2O + C6H8

Quantity Value Units Method Reference Comment
Deltar-0.84 ± 0.06kcal/molKinOth, Olsen, et al., 1977liquid phase; solvent: THF; At 452 K; ALS

1,3-Cyclohexadiene = 1,4-Cyclohexadiene

By formula: C6H8 = C6H8

Quantity Value Units Method Reference Comment
Deltar-0.4 ± 0.2kcal/molEqkTaskinen and Nummelin, 1986liquid phase; solvent: (CH3)2SO; GLC; ALS

1,3-Cyclohexadiene + Oxygen = Bicyclo[2.2.2]oct-5-ene-2,3-dione

By formula: C6H8 + O2 = C8H8O2

Quantity Value Units Method Reference Comment
Deltar-41.8 ± 4.8kcal/molCphaOlmsted, 1980liquid phase; solvent: CCl4; ALS

1,3-Cyclohexadiene + Tetracyanoethylene = Bicyclo[2.2.2]oct-5-ene-2,2,3,3-tetracarbonitrile

By formula: C6H8 + C6N4 = C12H8N4

Quantity Value Units Method Reference Comment
Deltar-28.90 ± 0.77kcal/molCmRogers, 1972liquid phase; ALS

Bicyclo[2.2.2]oct-5-ene-2,2,3,3-tetracarbonitrile = 1,3-Cyclohexadiene + Tetracyanoethylene

By formula: C12H8N4 = C6H8 + C6N4

Quantity Value Units Method Reference Comment
Deltar28.90 ± 0.77kcal/molCmRogers, 1972solid phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Steele, Chirico, et al., 1989
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K., Determination of some pure compound ideal-gas enthalpies of formation, AIChE Symp. Ser., 1989, 85, 140-162. [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]

Lenz T.G., 1989
Lenz T.G., Force-field calculations giving accurate conformation, Hf(T), S(T), and Cp(T) for unsaturated acyclic and cyclic hydrocarbons, J. Phys. Chem., 1989, 93, 1588-1592. [all data]

Geipel and Wolf, 1976
Geipel, G.; Wolf, G., Die molare Wärmekapazität von Cyclohexadien(1,4) und Cyclohexadien(1,3) im Temperaturegebiet von 10...300K, Z. Phys. Chem., 1976, 257, 587-593. [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]

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]

Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene, J. Am. Chem. Soc., 1936, 58, 146-153. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Huybrechts, Rigaux, et al., 1980
Huybrechts, G.; Rigaux, D.; Vankeerberghen, J.; Van Mele, B., Kinetics of the Diels-Alder addition of ethene to cyclohexa-1,3-diene and its reverse reaction in the gas phase, Int. J. Chem. Kinet., 1980, 12, 253-259. [all data]

Van Mele, Boon, et al., 1986
Van Mele, B.; Boon, G.; Huybrechts, G., Gas-phase kinetic and thermochemical data for endo- and exo-5-monosubstituted bicyclo[2.2.2]oct-2-enes, Int. J. Chem. Kinet., 1986, 18, 537-545. [all data]

Oth, Olsen, et al., 1977
Oth, J.F.M.; Olsen, H.; Synder, J.P., Energetics of heteroextrusion reactions. N2 vs. N2O, J. Am. Chem. Soc., 1977, 99, 8505-8507. [all data]

Taskinen and Nummelin, 1986
Taskinen, E.; Nummelin, K., Thermodynamics of vinyl ethers. 31. Isomer equilibria in some six- and seven-membered cyclic dienes, J. Org. Chem., 1986, 50, 4844-4847. [all data]

Olmsted, 1980
Olmsted, J., III, Photocalorimetric studies of singlet oxygen reactions, J. Am. Chem. Soc., 1980, 102, 66-71. [all data]

Rogers, 1972
Rogers, F.E., Thermochemistry of the Diels-Alder reactions. II. Heat of addition of several dienes to tetracyanoethylene, J. Phys. Chem., 1972, 76, 106-109. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References