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1,4-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), 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
Deltafgas24.00 ± 0.74kcal/molCcbLuk'yanova, Timofeeva, et al., 1991ALS
Deltafgas26.1kcal/molChydRoth, Adamczak, et al., 1991ALS
Deltafgas25.04 ± 0.14kcal/molCcrSteele, Chirico, et al., 1989ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
8.89650.Dorofeeva O.V., 1986GT
10.19100.
12.23150.
15.12200.
20.48273.15
22.48 ± 0.72298.15
22.63300.
30.533400.
37.481500.
43.253600.
48.026700.
52.015800.
55.380900.
58.2391000.
60.6761100.
62.7651200.
64.5581300.
66.1041400.
67.4431500.

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
Deltafliquid15.8 ± 0.74kcal/molCcbLuk'yanova, Timofeeva, et al., 1991ALS
Deltafliquid16.66 ± 0.14kcal/molCcrSteele, Chirico, et al., 1989ALS
Quantity Value Units Method Reference Comment
Deltacliquid-853.37 ± 0.72kcal/molCcbLuk'yanova, Timofeeva, et al., 1991Corresponding «DELTA»fliquid = 15.8 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-854.23 ± 0.11kcal/molCcrSteele, Chirico, et al., 1989Corresponding «DELTA»fliquid = 16.66 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid45.261cal/mol*KN/AGeipel and Wolf, 1976DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
33.99298.15Steele, Chirico, et al., 1989DH
34.880298.15Geipel 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
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
Tboil354.7KN/AAldrich Chemical Company Inc., 1990BS
Tboil362.70KN/AAnonymous, 1962Uncertainty assigned by TRC = 0.2 K; TRC
Tboil362.55KN/AAnonymous, 1942Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tfus222.83KN/AAnonymous, 1942Uncertainty assigned by TRC = 0.2 K; TRC
Tfus351.KN/AWhite and Bishop, 1940Crystal phase 1 phase; Uncertainty assigned by TRC = 4. K; TRC
Quantity Value Units Method Reference Comment
Ttriple224.0KN/AGeipel and Wolf, 1976, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Deltavap8.20kcal/molVLuk'yanova, Timofeeva, et al., 1991ALS
Deltavap8.20kcal/molN/ALuk'yanova, Timofeeva, et al., 1991DRB
Deltavap8.377 ± 0.01kcal/molVSteele, Chirico, et al., 1989ALS
Deltavap8.39kcal/molN/ASteele, Chirico, et al., 1989DRB

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
8.13319.AStephenson and Malanowski, 1987Based on data from 304. - 360. K.; AC
8.10308.MMLetcher and Marsicano, 1974Based on data from 304. - 322. K.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
1.37224.Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
1.02192.Domalski and Hearing, 1996CAL
6.097224.

Enthalpy of phase transition

DeltaHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.195192.0crystaline, IIcrystaline, IGeipel and Wolf, 1976DH
1.3660224.0crystaline, IliquidGeipel and Wolf, 1976DH

Entropy of phase transition

DeltaStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
1.02192.0crystaline, IIcrystaline, IGeipel and Wolf, 1976DH
6.097224.0crystaline, IliquidGeipel 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 by: 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

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
Deltar-53.90 ± 0.33kcal/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Glacial acetic acid

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

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
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 basicity193.1kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.82PEKimura, Katsumata, et al., 1981LLK
8.82 ± 0.02PEBieri, Burger, et al., 1977LLK
8.82 ± 0.02PIDemeo and El-Sayed, 1970RDSH
8.65 ± 0.05EIFranklin and Carroll, 1969RDSH
8.80PEBischof, Hashmall, et al., 1969RDSH
8.82PEKimura, Katsumata, et al., 1981Vertical value; LLK
8.82PEBock and Kaim, 1980Vertical value; LLK
8.80PEKobayashi, 1978Vertical value; LLK
8.82PEHeilbronner, Brogli, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H2+19.21 ± 0.15?EIFranklin and Carroll, 1969RDSH
C3H3+15.20 ± 0.10?EIFranklin and Carroll, 1969RDSH
C3H4+13.95 ± 0.10?EIFranklin and Carroll, 1969RDSH
C4H2+17.82 ± 0.25C2H2+2H2EIFranklin and Carroll, 1969RDSH
C4H3+17.08 ± 0.10C2H2+H2+H?EIFranklin and Carroll, 1969RDSH
C4H4+13.55 ± 0.10C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H5+14.48 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C4H6+12.17 ± 0.10C2H2EIFranklin and Carroll, 1969RDSH
C5H3+16.12 ± 0.10CH3+H2?EIFranklin and Carroll, 1969RDSH
C5H5+13.41 ± 0.10CH3EIFranklin and Carroll, 1969RDSH
C5H5+13.6CH3EIHarrison, Haynes, et al., 1965RDSH
C6H5+13.92 ± 0.10H2+HEIFranklin and Carroll, 1969RDSH
C6H6+9.61 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C6H6+9.86 ± 0.05H2EIFranklin and Carroll, 1969RDSH
C6H7+10.55HPIPECOLias and Ausloos, 1985LBLHLM
C6H7+10.94 ± 0.10HEIFranklin and Carroll, 1969RDSH

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, 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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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 114497

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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), Notes

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

Luk'yanova, Timofeeva, et al., 1991
Luk'yanova, V.A.; Timofeeva, L.P.; Kozina, M.P.; Kirin, V.N.; Tarakanova, A.V., Enthalpies of formation of certain unsaturated cyclic hydrocarbons, Russ. J. Phys. Chem. (Engl. Transl.), 1991, 65, 439-441. [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]

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]

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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Anonymous, 1962
Anonymous, R., , Am. Pet. Inst. Res. Proj. 58A, Annu. Rep., 1962. [all data]

Anonymous, 1942
Anonymous, R., , Am. Pet. Inst. Res. Proj. 6, Natl. Bur. Stand., 1942. [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]

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]

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]

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]

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]

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]

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]

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]

Bischof, Hashmall, et al., 1969
Bischof, P.; Hashmall, J.A.; Heilbronner, E.; Hornung, V., Photoelektronspektroskopische Bestimmung der Wechselwirkung zwischen nichtkonjugierten Doppelbindungen, Helv. Chim. Acta, 1969, 52, 1745. [all data]

Bock and Kaim, 1980
Bock, H.; Kaim, W., Radical ions. 37. Ionization and one-electron oxidation of electron-rich silylalkyl olefins, J. Am. Chem. Soc., 1980, 102, 4429. [all data]

Kobayashi, 1978
Kobayashi, T., A new rule for photoelectron angular distributions of molecules, Phys. Lett. A, 1978, 69, 31. [all data]

Heilbronner, Brogli, et al., 1976
Heilbronner, E.; Brogli, F.; Vogel, E., Photoelectron spectroscopic assignment of symmetry to the ground state and first excited state of the 1,4-cyclohexadiene radical cation, J. Electron Spectrosc. Relat. Phenom., 1976, 9, 227. [all data]

Harrison, Haynes, et al., 1965
Harrison, A.G.; Haynes, P.; McLean, S.; Meyer, F., The mass spectra of methyl-substituted cyclopentadienes, J. Am. Chem. Soc., 1965, 87, 5099. [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]


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), References