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
Δfgas25.00 ± 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.

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

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Individual Reactions

C6H7- + Hydrogen cation = 1,3-Cyclohexadiene

By formula: C6H7- + H+ = C6H8

Quantity Value Units Method Reference Comment
Δr373.2 ± 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
Δr365.8 ± 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
Δr-53.64 ± 0.29kcal/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Glacial acetic acid; ALS
Δr-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
Δr32.4kcal/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
Δr-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
Δr-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
Δr-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
Δr-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
Δr28.90 ± 0.77kcal/molCmRogers, 1972solid phase; ALS

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

View reactions leading to C6H8+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)200.kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity192.3kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.25PEKimura, Katsumata, et al., 1981LLK
8.25 ± 0.02PEBieri, Burger, et al., 1977LLK
8.25 ± 0.03PIDemeo and El-Sayed, 1970RDSH
8.25PEBischof and Heilbronner, 1970RDSH
8.28 ± 0.05EIFranklin and Carroll, 1969RDSH
8.32PEWorley, Webb, et al., 1979Vertical value; LLK
8.25 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H2+23.51 ± 0.50?EIFranklin and Carroll, 1969RDSH
C3H3+14.87 ± 0.10?EIFranklin and Carroll, 1969RDSH
C3H4+14.52 ± 0.10?EIFranklin and Carroll, 1969RDSH
C4H2+19.81 ± 0.10C2H2+2H2EIFranklin and Carroll, 1969RDSH
C4H3+17.62 ± 0.10C2H2+H2+H?EIFranklin and Carroll, 1969RDSH
C4H4+13.91 ± 0.20C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H5+14.69 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C4H6+12.60 ± 0.10C2H2EIFranklin and Carroll, 1969RDSH
C5H3+15.44 ± 0.10CH3+H2?EIFranklin and Carroll, 1969RDSH
C5H5+13.02 ± 0.10CH3EIFranklin and Carroll, 1969RDSH
C6H5+13.92 ± 0.10H2+HEIFranklin and Carroll, 1969RDSH
C6H6+10.12 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C6H6+9.88 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C6H7+10.45HPIPECOLias and Ausloos, 1985LBLHLM
C6H7+10.82 ± 0.10HEIFranklin and Carroll, 1969RDSH

De-protonation reactions

C6H7- + Hydrogen cation = 1,3-Cyclohexadiene

By formula: C6H7- + H+ = C6H8

Quantity Value Units Method Reference Comment
Δr373.2 ± 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
Δr365.8 ± 4.0kcal/molIMRBLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; B

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics 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]

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A., Ionization potential and structure of olefins, J. Chem. Phys., 1970, 52, 2622. [all data]

Bischof and Heilbronner, 1970
Bischof, P.; Heilbronner, E., Photoelektron-Spektren von Cycloalkenen und Cycloalkadienen, Helv. Chim. Acta, 1970, 53, 1677. [all data]

Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R., Effect of molecular structure on ionic decomposition. II. An electron-impact study of 1,3-and 1,4-cyclohexadiene and 1,3,5-hexatriene, J. Am. Chem. Soc., 1969, 91, 6564. [all data]

Worley, Webb, et al., 1979
Worley, S.D.; Webb, T.R.; Gibson, D.H.; Ong, T.-S., On the electronic structures of cyclobutadiene trimethylenemethane, J. Organomet. Chem., 1979, 168, 16. [all data]

Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K., Alkyl-induced, natural hypsochromic shifts of the 2A←2X and 2B←2X transitions of azulene and naphthalene radical cations, Nouv. J. Chim., 1976, 1, 105. [all data]

Lias and Ausloos, 1985
Lias, S.G.; Ausloos, P., Structures of C6H7+ ions formed in unimolecular and bimolecular reactions, J. Chem. Phys., 1985, 82, 3613. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References