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Cyclohexene

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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
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

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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
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

Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil356. ± 2.KAVGN/AAverage of 56 out of 57 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus169. ± 1.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple169.66KN/AHaida, Suga, et al., 1977, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple169.67KN/AHuffman, Eaton, et al., 1948, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC
Ttriple169.0KN/AParks and Huffman, 1930, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc560.4 ± 0.1KN/ATsonopoulos and Ambrose, 1996 
Tc560.4KN/AMajer and Svoboda, 1985 
Tc560.4KN/ACheng, McCoubrey, et al., 1962Uncertainty assigned by TRC = 0.3 K; Visual (5-cm 2-mm bore tubes) in nitrate-nitrite bath, TE or TH cal. vs NPL thermometer; TRC
Tc560.42KN/AAmbrose, Cox, et al., 1960Uncertainty assigned by TRC = 0.02 K; Visual, PRT, IPTS-48, with decomp.; TRC
Tc553.5KN/AAmbrose and Grant, 1957Uncertainty assigned by TRC = 0.15 K; TRC
Quantity Value Units Method Reference Comment
Deltavap33.57kJ/molN/AMajer and Svoboda, 1985 
Deltavap33.50 ± 0.53kJ/molVSteele, Chirico, et al., 1996ALS
Deltavap33.5kJ/molN/ASteele, Chirico, et al., 1996DRB
Deltavap33.5 ± 0.5kJ/molEBSteele, Chirico, et al., 1996Based on data from 285. - 357. K.; AC
Deltavap30.5 ± 0.3kJ/molVMathews, 1926ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
30.46356.2N/AMajer and Svoboda, 1985 
32.8330.N/AMarrufo, Aucejo, et al., 2009Based on data from 315. - 356. K.; AC
32.9325.N/ASteyer and Sundmacher, 2004Based on data from 310. - 356. K.; AC
32.6327.N/ASegura, Lam, et al., 2001Based on data from 312. - 356. K.; AC
32.7324.A,EBStephenson and Malanowski, 1987Based on data from 309. - 365. K. See also Meyer and Hotz, 1973.; AC
33.1308.MMLetcher and Marsicano, 1974Based on data from 305. - 322. K.; AC
32.7 ± 0.1313.CSvoboda, Veselý, et al., 1973AC
32.2 ± 0.1323.CSvoboda, Veselý, et al., 1973AC
31.7 ± 0.1333.CSvoboda, Veselý, et al., 1973AC
31.2 ± 0.1343.CSvoboda, Veselý, et al., 1973AC
30.7 ± 0.1353.CSvoboda, Veselý, et al., 1973AC
33.7300.MMForziati, Camin, et al., 1950Based on data from 285. - 357. K.; AC
32.59300.VLister, 1941Heat of bromination at 300 K; ALS
32.6300.N/ALister, 1941Based on data from 229. - 292. K.; AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kJ/mol) beta Tc (K) Reference Comment
313. - 353.47.190.2662560.4Majer and Svoboda, 1985 

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference
310.02 - 364.533.9973 ± 0.00181221.9 ± 1.0-49.98 ± 0.12Meyer and Hotz, 1973

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
3.28169.7Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
30.5138.7Domalski and Hearing, 1996CAL
19.35169.7

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.483112.3crystaline, IIIcrystaline, IHaida, Suga, et al., 1977DH
4.231138.63crystaline, IIcrystaline, IHaida, Suga, et al., 1977DH
3.284169.66crystaline, IliquidHaida, Suga, et al., 1977DH
4.2505138.7crystaline, IIcrystaline, IHuffman, Eaton, et al., 1948DH
3.2932169.67crystaline, IliquidHuffman, Eaton, et al., 1948DH
4.075138.7crystaline, IIcrystaline, IParks and Huffman, 1930DH
3.289169.0crystaline, IliquidParks and Huffman, 1930DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
13.2112.3crystaline, IIIcrystaline, IHaida, Suga, et al., 1977DH
30.52138.63crystaline, IIcrystaline, IHaida, Suga, et al., 1977DH
19.36169.66crystaline, IliquidHaida, Suga, et al., 1977DH
30.65138.7crystaline, IIcrystaline, IHuffman, Eaton, et al., 1948DH
19.41169.67crystaline, IliquidHuffman, Eaton, et al., 1948DH
29.38138.7crystaline, IIcrystaline, IParks and Huffman, 1930DH
19.46169.0crystaline, IliquidParks and Huffman, 1930DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1990.
NIST MS number 114431

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]

Haida, Suga, et al., 1977, 2
Haida, O.; Suga, H.; Seki, S., Calorimetric study of the glassy state. XI. Plural glass transition phenomena of cyclohexene, Bull. Chem. Soc. Jpn., 1977, 50, 802. [all data]

Huffman, Eaton, et al., 1948, 2
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. [all data]

Parks and Huffman, 1930, 2
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. [all data]

Tsonopoulos and Ambrose, 1996
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons, J. Chem. Eng. Data, 1996, 41, 645-656. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Cheng, McCoubrey, et al., 1962
Cheng, D.C.H.; McCoubrey, J.C.; Phillips, D.G., Critical Temperatures of Some Organic Cyclic Compounds, Trans. Faraday Soc., 1962, 58, 224. [all data]

Ambrose, Cox, et al., 1960
Ambrose, D.; Cox, J.D.; Townsend, R., The critical temperatures of forty organic compounds, Trans. Faraday Soc., 1960, 56, 1452. [all data]

Ambrose and Grant, 1957
Ambrose, D.; Grant, D.G., The Critical Temperatures of Some Hydrocarbons and Pyridine Bases, Trans. Faraday Soc., 1957, 53, 771. [all data]

Mathews, 1926
Mathews, J.H., The accurate measurement of heats of vaporization of liquids, J. Am. Chem. Soc., 1926, 48, 562-576. [all data]

Marrufo, Aucejo, et al., 2009
Marrufo, Beatriz; Aucejo, Antonio; Sanchotello, Margarita; Loras, Sonia, Isobaric vapor--liquid equilibrium for binary mixtures of 1-hexene+n-hexane and cyclohexane+cyclohexene at 30, 60 and 101.3kPa, Fluid Phase Equilibria, 2009, 279, 1, 11-16, https://doi.org/10.1016/j.fluid.2008.12.007 . [all data]

Steyer and Sundmacher, 2004
Steyer, Frank; Sundmacher, Kai, VLE and LLE Data for the System Cyclohexane + Cyclohexene + Water + Cyclohexanol, J. Chem. Eng. Data, 2004, 49, 6, 1675-1681, https://doi.org/10.1021/je049902w . [all data]

Segura, Lam, et al., 2001
Segura, Hugo; Lam, Elizabeth; Reich, Ricardo; Wisniak, Jaime, Isobaric Phase Equilibria in the Binary Systems Ethyl 1,1-Dimethylethyl Ether + 1-hexene and + Cyclohexene at 94.00 kPa, Physics and Chemistry of Liquids, 2001, 39, 1, 43-54, https://doi.org/10.1080/00319100108030325 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Meyer and Hotz, 1973
Meyer, Edwin F.; Hotz, Roger D., High-precision vapor-pressure data for eight organic compounds, J. Chem. Eng. Data, 1973, 18, 4, 359-362, https://doi.org/10.1021/je60059a008 . [all data]

Letcher and Marsicano, 1974
Letcher, T.M.; Marsicano, F., Vapour pressures and densities of some unsaturated C6 acyclic and cyclic hydrocarbons between 300 and 320 K, The Journal of Chemical Thermodynamics, 1974, 6, 5, 509-514, https://doi.org/10.1016/0021-9614(74)90013-5 . [all data]

Svoboda, Veselý, et al., 1973
Svoboda, V.; Veselý, F.; Holub, R.; Pick, J., Enthalpy data of liquids. II. The dependence of heats of vaporization of methanol, propanol, butanol, cyclohexane, cyclohexene, and benzene on temperature, Collect. Czech. Chem. Commun., 1973, 38, 12, 3539-3543, https://doi.org/10.1135/cccc19733539 . [all data]

Forziati, Camin, et al., 1950
Forziati, A.F.; Camin, D.L.; Rossini, F.D., Density, refractive index, boiling point, and vapor pressure of eight monoolefin (1-alkene), six pentadiene, and two cyclomonoolefin hydrocarbons, J. RES. NATL. BUR. STAN., 1950, 45, 5, 406, https://doi.org/10.6028/jres.045.044 . [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]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References