Cyclohexane

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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess

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

Cyclohexene + Hydrogen = Cyclohexane

By formula: C6H10 + H2 = C6H12

Quantity Value Units Method Reference Comment
Δr-28. ± 1.kcal/molAVGN/AAverage of 8 values; Individual data points

NH4+ + Cyclohexane = (NH4+ • Cyclohexane)

By formula: H4N+ + C6H12 = (H4N+ • C6H12)

Quantity Value Units Method Reference Comment
Δr9.kcal/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M
Quantity Value Units Method Reference Comment
Δr20.cal/mol*KN/ADeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
2.8317.PHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M

C6H6+ + Cyclohexane = (C6H6+ • Cyclohexane)

By formula: C6H6+ + C6H12 = (C6H6+ • C6H12)

Quantity Value Units Method Reference Comment
Δr11.2kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr27.cal/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
3.2295.PHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

C6H11- + Hydrogen cation = Cyclohexane

By formula: C6H11- + H+ = C6H12

Quantity Value Units Method Reference Comment
Δr418.3 ± 2.0kcal/molBranPeerboom, Rademaker, et al., 1992gas phase; B
Δr406.82 ± 0.90kcal/molG+TSBohme, Lee-Ruff, et al., 1972gas phase; B
Quantity Value Units Method Reference Comment
Δr409.5 ± 2.2kcal/molH-TSPeerboom, Rademaker, et al., 1992gas phase; B
Δr>398.00kcal/molIMRBBohme, Lee-Ruff, et al., 1972gas phase; 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

2Hydrogen + 1,4-Cyclohexadiene = Cyclohexane

By formula: 2H2 + C6H8 = C6H12

Quantity Value Units Method Reference Comment
Δr-55.6kcal/molChydRoth, Adamczak, et al., 1991liquid phase; ALS
Δr-53.90 ± 0.33kcal/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Glacial acetic acid; ALS

C3H9Si+ + Cyclohexane = (C3H9Si+ • Cyclohexane)

By formula: C3H9Si+ + C6H12 = (C3H9Si+ • C6H12)

Quantity Value Units Method Reference Comment
Δr37.9kcal/molPHPMSLi and Stone, 1989gas phase; condensation; M
Quantity Value Units Method Reference Comment
Δr48.1cal/mol*KPHPMSLi and Stone, 1989gas phase; condensation; M

3Hydrogen + Benzene = Cyclohexane

By formula: 3H2 + C6H6 = C6H12

Quantity Value Units Method Reference Comment
Δr-49.06 ± 0.15kcal/molChydKistiakowsky, Ruhoff, et al., 1936gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -49.80 ± 0.15 kcal/mol; At 355 °K; ALS

Hydrogen iodide + Cyclohexane, iodo- = Cyclohexane + Iodine

By formula: HI + C6H11I = C6H12 + I2

Quantity Value Units Method Reference Comment
Δr-7.8 ± 2.0kcal/molCmBrennan and Ubbelohde, 1956gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -6.8 ± 1.0 kcal/mol; ALS

Lithium ion (1+) + Cyclohexane = (Lithium ion (1+) • Cyclohexane)

By formula: Li+ + C6H12 = (Li+ • C6H12)

Quantity Value Units Method Reference Comment
Δr24.kcal/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M

Cyclopentane, methyl- = Cyclohexane

By formula: C6H12 = C6H12

Quantity Value Units Method Reference Comment
Δr-3.510kcal/molEqkGlasebrook and Lovell, 1939liquid phase; Heat of isomerization; ALS

2Hydrogen + Bicyclo[2.2.0]hex-1(4)-ene = Cyclohexane

By formula: 2H2 + C6H8 = C6H12

Quantity Value Units Method Reference Comment
Δr-102.0 ± 1.9kcal/molChydRoth, Adamczak, et al., 1991liquid phase; ALS

Cyclohexanol = Cyclohexane + Hydrogen

By formula: C6H12O = C6H12 + H2

Quantity Value Units Method Reference Comment
Δr15.2 ± 0.55kcal/molEqkFedoseenko, Yursha, et al., 1983gas phase; At 502 K; ALS

Cyclohexane, chloro- + Hydrogen chloride = Cyclohexane + Chlorine

By formula: C6H11Cl + HCl = C6H12 + Cl2

Quantity Value Units Method Reference Comment
Δr-34.20kcal/molCmKirkbride, 1956liquid phase; ALS

Cyclohexane = Cyclopentane, methyl-

By formula: C6H12 = C6H12

Quantity Value Units Method Reference Comment
Δr4.32 ± 0.28kcal/molEqkKabo and Andreevskii, 1973liquid phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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

Deakyne and Meot-Ner (Mautner), 1985
Deakyne, C.A.; Meot-Ner (Mautner), M., Unconventional Ionic Hydrogen Bonds. 2. NH+ pi. Complexes of Onium Ions with Olefins and Benzene Derivatives, J. Am. Chem. Soc., 1985, 107, 2, 474, https://doi.org/10.1021/ja00288a034 . [all data]

Meot-Ner (Mautner), Hamlet, et al., 1978
Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E.P.; Field, F.H., Bonding Energies in Association Ions of Aromatic Molecules. Correlations with Ionization Energies, J. Am. Chem. Soc., 1978, 100, 17, 5466, https://doi.org/10.1021/ja00485a034 . [all data]

Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [all data]

Bohme, Lee-Ruff, et al., 1972
Bohme, D.K.; Lee-Ruff, E.; Young, L.B., Acidity order of selected bronsted acids in the gas phase at 300K, J. Am. Chem. Soc., 1972, 94, 5153. [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]

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]

Li and Stone, 1989
Li, X.; Stone, J.A., Determination of the beta silicon effect from a mass spectrometric study of the association of trimethylsilylium ion with alkenes, J. Am. Chem. Soc., 1989, 111, 15, 5586, https://doi.org/10.1021/ja00197a013 . [all data]

Brennan and Ubbelohde, 1956
Brennan, D.; Ubbelohde, A.R., A thermochemical evaluation of bond strengths in some carbon compounds. Part IV. Bond-strength differences based on the reaction: RI + HI = RH + I2, where R = p-methoxyphenyl and cyclohexyl, J. Chem. Soc., 1956, 3011-3016. [all data]

Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [all data]

Glasebrook and Lovell, 1939
Glasebrook, A.L.; Lovell, W.G., The isomerization of cyclohexane and methylcyclopentane, J. Am. Chem. Soc., 1939, 61, 1717-1720. [all data]

Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions, Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [all data]

Kirkbride, 1956
Kirkbride, F.W., The heats of chlorination of some hydrocarbons and their chloro-derivatives, J. Appl. Chem., 1956, 6, 11-21. [all data]

Kabo and Andreevskii, 1973
Kabo, G.Ya.; Andreevskii, D.N., Thermodynamic characteristics of the cyclohexane = methylcyclopentane isomerization, Zh. Fiz. Khim., 1973, 47, 272-273. [all data]


Notes

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