Cyclohexene

Formula: C₆H₁₀
Molecular weight: 82.1436
IUPAC Standard InChI: InChI=1S/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2
IUPAC Standard InChIKey: HGCIXCUEYOPUTN-UHFFFAOYSA-N
CAS Registry Number: 110-83-8
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: Benzene tetrahydride; Benzene, tetrahydro-; Cyclohex-1-ene; Tetrahydrobenzene; 1,2,3,4-Tetrahydrobenzene; Cykloheksen; Hexanaphthylene; UN 2256; 1-Cyclohexene; NSC 24835
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
Data at other public NIST sites:
Options:
- Switch to SI units

Data at NIST subscription sites:

NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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.

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References, Notes

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
Δ_fH°_gas	-1.03 ± 0.23	kcal/mol	Ccr	Steele, Chirico, et al., 1996	ALS
Δ_fH°_gas	-1.1	kcal/mol	N/A	Good and Smith, 1969	Value computed using Δ_fH_liquid° value of -38.2±0.6 kj/mol from Good and Smith, 1969 and Δ_vapH° value of 33.5 kj/mol from Steele, Chirico, et al., 1996.; DRB
Δ_fH°_gas	-1.3	kcal/mol	N/A	Labbauf and Rossini, 1961	Value computed using Δ_fH_liquid° value of -38.8±0.6 kj/mol from Labbauf and Rossini, 1961 and Δ_vapH° value of 33.5 kj/mol from Steele, Chirico, et al., 1996.; DRB
Δ_fH°_gas	-1.7	kcal/mol	N/A	Epstein, Pitzer, et al., 1949	Value computed using Δ_fH_liquid° value of -40.6±0.8 kj/mol from Epstein, Pitzer, et al., 1949 and Δ_vapH° value of 33.5 kj/mol from Steele, Chirico, et al., 1996.; DRB
Quantity	Value	Units	Method	Reference	Comment
S°_gas	74.199	cal/mol*K	N/A	Beckett C.W., 1948	GT

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
8.394	50.	Dorofeeva O.V., 1986	Recommended 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
10.29	100.
12.85	150.
16.10	200.
22.02	273.15
24.25 ± 0.72	298.15
24.417	300.
33.389	400.
41.413	500.
48.145	600.
53.755	700.
58.473	800.
62.471	900.
65.877	1000.
68.793	1100.
71.293	1200.
73.444	1300.
75.301	1400.
76.907	1500.

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
31.900	370.	Montgomery J.B., 1942	GT
33.800	390.
35.500	410.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References, Notes

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
Δ_fH°_liquid	-9.0 ± 2.0	kcal/mol	Ccr	Steele, Chirico, et al., 1996	ALS
Δ_fH°_liquid	-9.13 ± 0.14	kcal/mol	Ccb	Good and Smith, 1969	ALS
Δ_fH°_liquid	-9.28 ± 0.14	kcal/mol	Ccb	Labbauf and Rossini, 1961	ALS
Δ_fH°_liquid	-9.70 ± 0.19	kcal/mol	Ccb	Epstein, Pitzer, et al., 1949	Unpublished results; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-896.84 ± 0.12	kcal/mol	Ccr	Steele, Chirico, et al., 1996	Corresponding Δ_fHº_liquid = -9.039 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-896.75 ± 0.12	kcal/mol	Ccb	Good and Smith, 1969	Corresponding Δ_fHº_liquid = -9.13 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-896.62 ± 0.12	kcal/mol	Ccb	Labbauf and Rossini, 1961	Corresponding Δ_fHº_liquid = -9.26 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-898.8	kcal/mol	Ccb	Konovalon, 1926	Heat of combustion at 15°C; Corresponding Δ_fHº_liquid = -7.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	51.291	cal/mol*K	N/A	Haida, Suga, et al., 1977	DH
S°_liquid	51.671	cal/mol*K	N/A	Huffman, Eaton, et al., 1948	DH
S°_liquid	51.79	cal/mol*K	N/A	Parks and Huffman, 1930	Extrapolation below 90 K, 49.20 J/mol*K.; DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
35.56	298.15	Steele, Chirico, et al., 1993	DH
36.544	298.12	Kalinowska and Woycicki, 1988	T = 183 to 298 K. Unsmoothed experimental datum.; DH
35.457	298.15	Haida, Suga, et al., 1977	T = 15 to 293 K.; DH
35.650	298.15	Huffman, Eaton, et al., 1948	T = 12 to 300 K.; DH
34.80	293.2	Parks and Huffman, 1930	T = 92 to 293 K. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Henry's Law data, References, Notes

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 + =

By formula: C₆H₁₀ + H₂ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-28. ± 1.	kcal/mol	AVG	N/A	Average of 8 values; Individual data points

C₆H₉^- + = Cyclohexene

By formula: C₆H₉^- + H⁺ = C₆H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	386.5 ± 5.1	kcal/mol	G+TS	Lee and Squires, 1986	gas phase; Between H2O, MeOH; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	379.0 ± 5.0	kcal/mol	IMRB	Lee and Squires, 1986	gas phase; Between H2O, MeOH; B

C₃H₉Si⁺ + Cyclohexene = (C₃H₉Si⁺ • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	32.9	kcal/mol	PHPMS	Li and Stone, 1989	gas phase; condensation; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	45.6	cal/mol*K	PHPMS	Li and Stone, 1989	gas phase; condensation; M

CH₆N⁺ + Cyclohexene = (CH₆N⁺ • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	11.6	kcal/mol	PHPMS	Deakyne and Meot-Ner (Mautner), 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	16.9	cal/mol*K	PHPMS	Deakyne and Meot-Ner (Mautner), 1985	gas phase; M

Cyclohexene + =

By formula: C₆H₁₀ + C₂HF₃O₂ = C₈H₁₁F₃O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-10.36 ± 0.03	kcal/mol	Cac	Wiberg, Wasserman, et al., 1985	liquid phase; solvent: Trifluoroacetic acid; Triflouroacetolysis; ALS

Cyclohexene + =

By formula: C₆H₁₀ + Br₂ = C₆H₁₀Br₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-33.630	kcal/mol	Cm	Lister, 1941	gas phase; Heat of bromination at 300 K; ALS

Henry's Law data

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

Data compiled by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

k°_H (mol/(kg*bar))	Method	Reference	Comment
0.026	M	N/A
0.022	Q	N/A	missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.022	V	N/A

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Notes

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, Henry's Law data, References

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
S°_gas	Entropy of gas at standard conditions
S°_liquid	Entropy of liquid at standard conditions
d(ln(k_H))/d(1/T)	Temperature dependence parameter for Henry's Law constant
k°_H	Henry's Law constant at 298.15K
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
Customer support for NIST Standard Reference Data products.