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1,3-Cyclohexadiene

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas25.00 ± 0.15kcal/molCcrSteele, Chirico, et al., 1989ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
8.18450.Dorofeeva O.V., 1986Recommended entropy values at 298.15 and 1000 K are less than those obtained by force-field calculation [ Lenz T.G., 1989] by 6.6 and 5.0 J/mol*K, respectively. Discrepancies between Cp(T) values amount to about 3 J/mol*K.; GT
9.747100.
12.01150.
15.00200.
20.47273.15
22.51 ± 0.60298.15
22.66300.
30.724400.
37.761500.
43.556600.
48.313700.
52.271800.
55.600900.
58.4251000.
60.8341100.
62.8971200.
64.6701300.
66.2001400.
67.5241500.

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
Deltafliquid17.07 ± 0.15kcal/molCcrSteele, Chirico, et al., 1989ALS
Quantity Value Units Method Reference Comment
Deltacliquid-854.63 ± 0.13kcal/molCcrSteele, Chirico, et al., 1989Corresponding «DELTA»fliquid = 17.07 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid47.151cal/mol*KN/AGeipel and Wolf, 1976DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
33.77298.15Steele, Chirico, et al., 1989DH
34.551298.15Geipel and Wolf, 1976T = 10 to 300 K.; 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil354. ± 2.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus184.KN/AWhite and Bishop, 1940Crystal phase 1 phase; Uncertainty assigned by TRC = 4. K; TRC
Tfus168.4KN/AKistiakowsky, Ruhoff, et al., 1936Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Ttriple161.0KN/AGeipel and Wolf, 1976, 2Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Deltavap7.93 ± 0.01kcal/molVSteele, Chirico, et al., 1989ALS
Deltavap7.93kcal/molN/ASteele, Chirico, et al., 1989DRB
Deltavap7.9kcal/molVRogers, 1972ALS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
7.79322.A,EBStephenson and Malanowski, 1987Based on data from 307. - 364. K. See also Meyer and Hotz, 1973.; AC
7.74308.MMLetcher and Marsicano, 1974Based on data from 304. - 322. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference
307.33 - 363.313.98464 ± 0.000481206.00 ± 0.87-50.83 ± 0.10Meyer and Hotz, 1973

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
1.0049161.0Geipel and Wolf, 1976DH
1.0161.Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
6.240161.0Geipel and Wolf, 1976DH

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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C6H7- + Hydrogen cation = 1,3-Cyclohexadiene

By formula: C6H7- + H+ = C6H8

Quantity Value Units Method Reference Comment
Deltar373.2 ± 4.1kcal/molG+TSLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar365.8 ± 4.0kcal/molIMRBLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; 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., 1936, 2gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -55.4 ± 0.1 kcal/mol; At 355 °K; ALS

Bicyclo[2.2.2]oct-2-ene = 1,3-Cyclohexadiene + Ethylene

By formula: C8H12 = C6H8 + C2H4

Quantity Value Units Method Reference Comment
Deltar32.4kcal/molKinHuybrechts, Rigaux, et al., 1980gas phase; Diels-Alder addition at 560°K, see Van Mele, Boon, et al., 1986; ALS

2,3-Diazabicyclo[2.2.2]octa-2,5-diene N-oxide = Nitrous oxide + 1,3-Cyclohexadiene

By formula: C6H8N2O = N2O + C6H8

Quantity Value Units Method Reference Comment
Deltar-0.84 ± 0.06kcal/molKinOth, Olsen, et al., 1977liquid phase; solvent: THF; At 452 K; ALS

1,3-Cyclohexadiene = 1,4-Cyclohexadiene

By formula: C6H8 = C6H8

Quantity Value Units Method Reference Comment
Deltar-0.4 ± 0.2kcal/molEqkTaskinen and Nummelin, 1986liquid phase; solvent: (CH3)2SO; GLC; ALS

1,3-Cyclohexadiene + Oxygen = Bicyclo[2.2.2]oct-5-ene-2,3-dione

By formula: C6H8 + O2 = C8H8O2

Quantity Value Units Method Reference Comment
Deltar-41.8 ± 4.8kcal/molCphaOlmsted, 1980liquid phase; solvent: CCl4; ALS

1,3-Cyclohexadiene + Tetracyanoethylene = Bicyclo[2.2.2]oct-5-ene-2,2,3,3-tetracarbonitrile

By formula: C6H8 + C6N4 = C12H8N4

Quantity Value Units Method Reference Comment
Deltar-28.90 ± 0.77kcal/molCmRogers, 1972liquid phase; ALS

Bicyclo[2.2.2]oct-5-ene-2,2,3,3-tetracarbonitrile = 1,3-Cyclohexadiene + Tetracyanoethylene

By formula: C12H8N4 = C6H8 + C6N4

Quantity Value Units Method Reference Comment
Deltar28.90 ± 0.77kcal/molCmRogers, 1972solid phase; ALS

Gas phase ion energetics data

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

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

View reactions leading to C6H8+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)200.kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity192.3kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.25PEKimura, Katsumata, et al., 1981LLK
8.25 ± 0.02PEBieri, Burger, et al., 1977LLK
8.25 ± 0.03PIDemeo and El-Sayed, 1970RDSH
8.25PEBischof and Heilbronner, 1970RDSH
8.28 ± 0.05EIFranklin and Carroll, 1969RDSH
8.32PEWorley, Webb, et al., 1979Vertical value; LLK
8.25 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H2+23.51 ± 0.50?EIFranklin and Carroll, 1969RDSH
C3H3+14.87 ± 0.10?EIFranklin and Carroll, 1969RDSH
C3H4+14.52 ± 0.10?EIFranklin and Carroll, 1969RDSH
C4H2+19.81 ± 0.10C2H2+2H2EIFranklin and Carroll, 1969RDSH
C4H3+17.62 ± 0.10C2H2+H2+H?EIFranklin and Carroll, 1969RDSH
C4H4+13.91 ± 0.20C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H5+14.69 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C4H6+12.60 ± 0.10C2H2EIFranklin and Carroll, 1969RDSH
C5H3+15.44 ± 0.10CH3+H2?EIFranklin and Carroll, 1969RDSH
C5H5+13.02 ± 0.10CH3EIFranklin and Carroll, 1969RDSH
C6H5+13.92 ± 0.10H2+HEIFranklin and Carroll, 1969RDSH
C6H6+10.12 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C6H6+9.88 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C6H7+10.45HPIPECOLias and Ausloos, 1985LBLHLM
C6H7+10.82 ± 0.10HEIFranklin and Carroll, 1969RDSH

De-protonation reactions

C6H7- + Hydrogen cation = 1,3-Cyclohexadiene

By formula: C6H7- + H+ = C6H8

Quantity Value Units Method Reference Comment
Deltar373.2 ± 4.1kcal/molG+TSLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar365.8 ± 4.0kcal/molIMRBLee and Squires, 1986gas phase; Between SiH4, tBuOH; value altered from reference due to change in acidity scale; B

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)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, References, Notes

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 118700

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.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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 by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Piliugin, Opanasenko, et al., 1958
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 5944
Instrument Spectrophotometer SF-4
Melting point -89
Boiling point 80.5

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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., 1989
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K., Determination of some pure compound ideal-gas enthalpies of formation, AIChE Symp. Ser., 1989, 85, 140-162. [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]

Lenz T.G., 1989
Lenz T.G., Force-field calculations giving accurate conformation, Hf(T), S(T), and Cp(T) for unsaturated acyclic and cyclic hydrocarbons, J. Phys. Chem., 1989, 93, 1588-1592. [all data]

Geipel and Wolf, 1976
Geipel, G.; Wolf, G., Die molare Wärmekapazität von Cyclohexadien(1,4) und Cyclohexadien(1,3) im Temperaturegebiet von 10...300K, Z. Phys. Chem., 1976, 257, 587-593. [all data]

White and Bishop, 1940
White, A.H.; Bishop, W.S., Dielectric Evidence of Molecular Rotation in the Crystals of Certain Non-aromatic Compounds, J. Am. Chem. Soc., 1940, 62, 8-16. [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, 146-53. [all data]

Geipel and Wolf, 1976, 2
Geipel, G.; Wolf, G., Molar Heat Capacity of Cyclohexadiene(1,4) and Cyclohexadiene(1,3) in Temperature Range of 10... 300K, Z. Phys. Chem. (Leipzig), 1976, 257, 587. [all data]

Rogers, 1972
Rogers, F.E., Thermochemistry of the Diels-Alder reactions. II. Heat of addition of several dienes to tetracyanoethylene, J. Phys. Chem., 1972, 76, 106-109. [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]

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]

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, 2
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]

Huybrechts, Rigaux, et al., 1980
Huybrechts, G.; Rigaux, D.; Vankeerberghen, J.; Van Mele, B., Kinetics of the Diels-Alder addition of ethene to cyclohexa-1,3-diene and its reverse reaction in the gas phase, Int. J. Chem. Kinet., 1980, 12, 253-259. [all data]

Van Mele, Boon, et al., 1986
Van Mele, B.; Boon, G.; Huybrechts, G., Gas-phase kinetic and thermochemical data for endo- and exo-5-monosubstituted bicyclo[2.2.2]oct-2-enes, Int. J. Chem. Kinet., 1986, 18, 537-545. [all data]

Oth, Olsen, et al., 1977
Oth, J.F.M.; Olsen, H.; Synder, J.P., Energetics of heteroextrusion reactions. N2 vs. N2O, J. Am. Chem. Soc., 1977, 99, 8505-8507. [all data]

Taskinen and Nummelin, 1986
Taskinen, E.; Nummelin, K., Thermodynamics of vinyl ethers. 31. Isomer equilibria in some six- and seven-membered cyclic dienes, J. Org. Chem., 1986, 50, 4844-4847. [all data]

Olmsted, 1980
Olmsted, J., III, Photocalorimetric studies of singlet oxygen reactions, J. Am. Chem. Soc., 1980, 102, 66-71. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A., Ionization potential and structure of olefins, J. Chem. Phys., 1970, 52, 2622. [all data]

Bischof and Heilbronner, 1970
Bischof, P.; Heilbronner, E., Photoelektron-Spektren von Cycloalkenen und Cycloalkadienen, Helv. Chim. Acta, 1970, 53, 1677. [all data]

Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R., Effect of molecular structure on ionic decomposition. II. An electron-impact study of 1,3-and 1,4-cyclohexadiene and 1,3,5-hexatriene, J. Am. Chem. Soc., 1969, 91, 6564. [all data]

Worley, Webb, et al., 1979
Worley, S.D.; Webb, T.R.; Gibson, D.H.; Ong, T.-S., On the electronic structures of cyclobutadiene trimethylenemethane, J. Organomet. Chem., 1979, 168, 16. [all data]

Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K., Alkyl-induced, natural hypsochromic shifts of the 2A<--2X and 2B<--2X transitions of azulene and naphthalene radical cations, Nouv. J. Chim., 1976, 1, 105. [all data]

Lias and Ausloos, 1985
Lias, S.G.; Ausloos, P., Structures of C6H7+ ions formed in unimolecular and bimolecular reactions, J. Chem. Phys., 1985, 82, 3613. [all data]

Piliugin, Opanasenko, et al., 1958
Piliugin, G.T.; Opanasenko, E.P.; Shinkorenko, S.V., Research in the field of synthetic dyestuffs. X. Synthesis of n-aryl-2-«beta»-anilinovinylquinoline derivatives and their transformations, Zh. Obshch. Khim., 1958, 28, 1374-1377. [all data]


Notes

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