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Cyclohexene

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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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-4.32 ± 0.98kJ/molCcrSteele, Chirico, et al., 1996ALS
Deltafgas-4.7kJ/molN/AGood and Smith, 1969Value computed using «DELTA»fHliquid° value of -38.2±0.6 kj/mol from Good and Smith, 1969 and «DELTA»vapH° value of 33.5 kj/mol from Steele, Chirico, et al., 1996.; DRB
Deltafgas-5.3kJ/molN/ALabbauf and Rossini, 1961Value computed using «DELTA»fHliquid° value of -38.8±0.6 kj/mol from Labbauf and Rossini, 1961 and «DELTA»vapH° value of 33.5 kj/mol from Steele, Chirico, et al., 1996.; DRB
Deltafgas-7.1kJ/molN/AEpstein, Pitzer, et al., 1949Value computed using «DELTA»fHliquid° value of -40.6±0.8 kj/mol from Epstein, Pitzer, et al., 1949 and «DELTA»vapH° value of 33.5 kj/mol from Steele, Chirico, et al., 1996.; DRB
Quantity Value Units Method Reference Comment
gas310.45J/mol*KN/ABeckett C.W., 1948GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
35.1250.Dorofeeva O.V., 1986Recommended S(298.15 K) value agrees well with experimental one [ Beckett C.W., 1948], however calculated Cp(T) values are about 5 J/mol*K lower than those obtained from experimental measurements [ Montgomery J.B., 1942]. To fit calculated Cp(T) values to experiment, [ Beckett C.W., 1948] suggested existence of stable half-boat conformation. This suggestion was found to be incorrect later. [ Dorofeeva O.V., 1986] used more reliable data on molecular structure and their S(T) and Cp(T) values are in good agreement with results of detail force-field calculations [ Lenz T.G., 1990].; GT
43.06100.
53.78150.
67.35200.
92.14273.15
101.5 ± 3.0298.15
102.16300.
139.70400.
173.27500.
201.44600.
224.91700.
244.65800.
261.38900.
275.631000.
287.831100.
298.291200.
307.291300.
315.061400.
321.781500.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
133.47370.Montgomery J.B., 1942GT
141.42390.
148.53410.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-37.8 ± 8.2kJ/molCcrSteele, Chirico, et al., 1996ALS
Deltafliquid-38.2 ± 0.59kJ/molCcbGood and Smith, 1969ALS
Deltafliquid-38.8 ± 0.59kJ/molCcbLabbauf and Rossini, 1961ALS
Deltafliquid-40.6 ± 0.79kJ/molCcbEpstein, Pitzer, et al., 1949Unpublished results; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3752.39 ± 0.49kJ/molCcrSteele, Chirico, et al., 1996Corresponding «DELTA»fliquid = -37.82 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-3752.0 ± 0.50kJ/molCcbGood and Smith, 1969Corresponding «DELTA»fliquid = -38.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-3751.5 ± 0.50kJ/molCcbLabbauf and Rossini, 1961Corresponding «DELTA»fliquid = -38.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-3761.kJ/molCcbKonovalon, 1926Heat of combustion at 15°C; Corresponding «DELTA»fliquid = -30. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid214.60J/mol*KN/AHaida, Suga, et al., 1977DH
liquid216.19J/mol*KN/AHuffman, Eaton, et al., 1948DH
liquid216.7J/mol*KN/AParks and Huffman, 1930Extrapolation below 90 K, 49.20 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
148.8298.15Steele, Chirico, et al., 1993DH
152.90298.12Kalinowska and Woycicki, 1988T = 183 to 298 K. Unsmoothed experimental datum.; DH
148.35298.15Haida, Suga, et al., 1977T = 15 to 293 K.; DH
149.16298.15Huffman, Eaton, et al., 1948T = 12 to 300 K.; DH
145.6293.2Parks and Huffman, 1930T = 92 to 293 K. Value is unsmoothed experimental datum.; 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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-118. ± 6.kJ/molAVGN/AAverage of 8 values; Individual data points

C6H9- + Hydrogen cation = Cyclohexene

By formula: C6H9- + H+ = C6H10

Quantity Value Units Method Reference Comment
Deltar1617. ± 21.kJ/molG+TSLee and Squires, 1986gas phase; Between H2O, MeOH; B
Quantity Value Units Method Reference Comment
Deltar1586. ± 21.kJ/molIMRBLee and Squires, 1986gas phase; Between H2O, MeOH; B

C3H9Si+ + Cyclohexene = (C3H9Si+ bullet Cyclohexene)

By formula: C3H9Si+ + C6H10 = (C3H9Si+ bullet C6H10)

Quantity Value Units Method Reference Comment
Deltar138.kJ/molPHPMSLi and Stone, 1989gas phase; condensation; M
Quantity Value Units Method Reference Comment
Deltar191.J/mol*KPHPMSLi and Stone, 1989gas phase; condensation; M

CH6N+ + Cyclohexene = (CH6N+ bullet Cyclohexene)

By formula: CH6N+ + C6H10 = (CH6N+ bullet C6H10)

Quantity Value Units Method Reference Comment
Deltar48.5kJ/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar70.7J/mol*KPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M

Cyclohexene + Trifluoroacetic acid = Acetic acid, trifluoro-, cyclohexyl ester

By formula: C6H10 + C2HF3O2 = C8H11F3O2

Quantity Value Units Method Reference Comment
Deltar-43.3 ± 0.1kJ/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Triflouroacetolysis; ALS

Cyclohexene + Bromine = Cyclohexane, 1,2-dibromo-

By formula: C6H10 + Br2 = C6H10Br2

Quantity Value Units Method Reference Comment
Deltar-140.71kJ/molCmLister, 1941gas phase; Heat of bromination at 300 K; 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., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K.; Tasker, I.R., Thermodynamic properties and ideal-gas enthalpies of formation for cyclohexene, phthalan (2,5-dihydrobenzo-3,4-furan), isoxazole, octylamine, dioctylamine, trioctylamine, phenyl isocyanate, and 1,4,5,6-tetrahydropyrimidine, J. Chem. Eng. Data, 1996, 41, 1269-1284. [all data]

Good and Smith, 1969
Good, W.D.; Smith, N.K., Enthalpies of combustion of toluene, benzene, cyclohexane, cyclohexene, methylcyclopentane, 1-methylcyclopentene, and n-hexane, J. Chem. Eng. Data, 1969, 14, 102-106. [all data]

Labbauf and Rossini, 1961
Labbauf, A.; Rossini, F.D., Heats of combustion, formation, and hydrogenation of 14 selected cyclomonoolefin hydrocarbons, J. Phys. Chem., 1961, 65, 476-480. [all data]

Epstein, Pitzer, et al., 1949
Epstein, M.B.; Pitzer, K.S.; Rossini, F.D., Heats, equilibrium constants, and free energies of formation of cyclopentene and cyclohexene, J. Res. NBS, 1949, 42, 379-382. [all data]

Beckett C.W., 1948
Beckett C.W., The thermodynamic properties and molecular structure of cyclopentene and cyclohexene, J. Am. Chem. Soc., 1948, 70, 4227-4230. [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]

Montgomery J.B., 1942
Montgomery J.B., The heat capacity of organic vapors. IV. Benzene, fluorobenzene, toluene, cyclohexane, methylcyclohexane and cyclohexene, J. Am. Chem. Soc., 1942, 64, 2375-2377. [all data]

Lenz T.G., 1990
Lenz T.G., Force field calculation of equilibrium thermodynamic properties: Diels-Alder reaction of 1,3-butadiene and ethylene and Diels-Alder dimerization of 1,3-butadiene, J. Comput. Chem., 1990, 11, 351-360. [all data]

Konovalon, 1926
Konovalon, D.-P., Sur Les Chaleurs de Combustion de Quelques hydrocarbures cycliques, J. Chim. Phys., 1926, 23, 359-362. [all data]

Haida, Suga, et al., 1977
Haida, O.; Suga, H.; Seki, S., Calorimetric study of the glassy state. XI. Plural glass-transition phenomena of cyclohexene, Bull. Chem. Soc. Japan, 1977, 50, 802-809. [all data]

Huffman, Eaton, et al., 1948
Huffman, H.M.; Eaton, M.; Oliver, G.D., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentene and cyclohexene, J. Am. Chem. Soc., 1948, 70, 2911-2914. [all data]

Parks and Huffman, 1930
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IX. A study of the effect of unsaturation on the heat capacities, entropies and free energies of some hydrocarbons and other compounds, J. Am. Chem. Soc., 1930, 52, 4381-4391. [all data]

Steele, Chirico, et al., 1993
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Tasker, I.R., Determination of ideal gas enthalpies of formation for key compounds the 1991 project results, DIPPR Project, 1993, 871, NIPER-716. [all data]

Kalinowska and Woycicki, 1988
Kalinowska, B.; Woycicki, W., Heat capacities and excess heat capacities of (an alkanol + an unsaturated hydrocarbon). II. (Propan-1-ol + cyclohexene), J. Chem. Thermodynam., 1988, 20, 1131-1135. [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]

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]

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]

Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A., Enthalpies of hydration of alkenes. 3. Cycloalkenes, J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]

Lister, 1941
Lister, M.W., Heats of organic reactions. X. Heats of bromination of cyclic olefins, J. Am. Chem. Soc., 1941, 63, 143-149. [all data]


Notes

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