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1,3-Cyclohexadiene

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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 - J.E. Bartmess
ALS - H.Y. Afeefy, J.F. Liebman, and S.E. Stein

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Individual Reactions

C6H7- + Hydrogen cation = 1,3-Cyclohexadiene

By formula: C6H7- + H+ = C6H8

Quantity Value Units Method Reference Comment
Deltar1561. ± 17.kJ/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
Deltar1531. ± 17.kJ/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-224.4 ± 1.2kJ/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Glacial acetic acid; ALS
Deltar-229.6 ± 0.42kJ/molChydKistiakowsky, Ruhoff, et al., 1936gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -231.7 ± 0.4 kJ/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
Deltar136.kJ/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-3.5 ± 0.3kJ/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-1.6 ± 0.8kJ/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-175. ± 20.kJ/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-120.9 ± 3.2kJ/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
Deltar120.9 ± 3.2kJ/molCmRogers, 1972solid phase; ALS

References

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

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

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