Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

Cyclohexane

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.


Reaction thermochemistry data

Go To: Top, 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
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
Deltar-28. ± 1.kcal/molAVGN/AAverage of 8 values; Individual data points

NH4+ + Cyclohexane = (NH4+ bullet Cyclohexane)

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

Quantity Value Units Method Reference Comment
Deltar9.kcal/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated, DG<, «DELTA»rH<; M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/ADeakyne and Meot-Ner (Mautner), 1985gas phase; Entropy change calculated or estimated, DG<, «DELTA»rH<; M

Free energy of reaction

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

C6H6+ + Cyclohexane = (C6H6+ bullet Cyclohexane)

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

Quantity Value Units Method Reference Comment
Deltar11.2kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar27.cal/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (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
Deltar418.3 ± 2.0kcal/molBranPeerboom, Rademaker, et al., 1992gas phase; B
Deltar406.82 ± 0.90kcal/molG+TSBohme, Lee-Ruff, et al., 1972gas phase; B
Quantity Value Units Method Reference Comment
Deltar409.5 ± 2.2kcal/molH-TSPeerboom, Rademaker, et al., 1992gas phase; B
Deltar>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
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

2Hydrogen + 1,4-Cyclohexadiene = Cyclohexane

By formula: 2H2 + C6H8 = C6H12

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

C3H9Si+ + Cyclohexane = (C3H9Si+ bullet Cyclohexane)

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

Quantity Value Units Method Reference Comment
Deltar37.9kcal/molPHPMSLi and Stone, 1989gas phase; condensation; M
Quantity Value Units Method Reference Comment
Deltar48.1cal/mol*KPHPMSLi and Stone, 1989gas phase; condensation; M

3Hydrogen + Benzene = Cyclohexane

By formula: 3H2 + C6H6 = C6H12

Quantity Value Units Method Reference Comment
Deltar-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
Deltar-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+) bullet Cyclohexane)

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

Quantity Value Units Method Reference Comment
Deltar24.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
Deltar-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
Deltar-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
Deltar15.2 ± 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
Deltar-34.20kcal/molCmKirkbride, 1956liquid phase; ALS

Cyclohexane = Cyclopentane, methyl-

By formula: C6H12 = C6H12

Quantity Value Units Method Reference Comment
Deltar4.32 ± 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

Go To: Top, Reaction thermochemistry data, References