1,5-Hexadiene


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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas20.4 ± 0.4kcal/molChydFang and Rogers, 1992 

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
Δcliquid-918.81 ± 0.07kcal/molCmCoops, Mulder, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = -918.44 ± 0.07 kcal/mol; Corresponding Δfliquid = 12.93 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-927.5kcal/molCcbClopatt, 1932Corresponding Δfliquid = 21.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Δcsolid-926.0kcal/molCcbHandrick, 1956Kogerman, P. N., 1934; Corresponding Δfsolid = 20.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
31.81298.von Reis, 1881T = 291 to 328 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
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil333. ± 1.KAVGN/AAverage of 14 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus132.3 ± 0.4KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Tc508.KN/ATsonopoulos and Ambrose, 1996 

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
7.03314.AStephenson and Malanowski, 1987Based on data from 299. to 333. K.; AC
7.29288.AStephenson and Malanowski, 1987Based on data from 273. to 333. K. See also Bevan, Malkin, et al., 1955 and Dykyj, 1972.; AC
6.84308.N/ALetcher and Marsicano, 1974Based on data from 300. to 319. 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 Comment
273.19 to 332.43.682511008.139-58.987Cummings and McLaughlin, 1955Coefficents calculated by NIST from author's data.

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 + 1,5-Hexadiene = n-Hexane

By formula: 2H2 + C6H10 = C6H14

Quantity Value Units Method Reference Comment
Δr-60.3 ± 0.4kcal/molChydFang and Rogers, 1992liquid phase; solvent: Cyclohexane
Δr-60.69 ± 0.65kcal/molChydMolnar, Rachford, et al., 1984liquid phase; solvent: Dioxane
Δr-60.17 ± 0.37kcal/molChydTurner, Mallon, et al., 1973liquid phase; solvent: Glacial acetic acid
Δr-60.03 ± 0.10kcal/molChydKistiakowsky, Ruhoff, et al., 1936gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -60.53 ± 0.15 kcal/mol; At 355 °K

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

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

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference
0.0074 VN/A

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:
L - 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

View reactions leading to C6H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.27 ± 0.05eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
9.29 ± 0.05EIWolkoff, Holmes, et al., 1980LLK
9.29EILossing and Traeger, 1975LLK
9.25PEMartin, Heller, et al., 1980Vertical value; LLK
9.59 ± 0.02PEBunzli, Burak, et al., 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H5+>10.9?EIHart and Friedli, 1970RDSH
C5H7+9.35 ± 0.05CH3EIWolkoff, Holmes, et al., 1980LLK
C5H7+9.29CH3EILossing and Traeger, 1975, 2LLK
C5H7+9.35CH3EILossing and Traeger, 1975LLK

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 Japan AIST/NIMC Database- Spectrum MS-NW-1213
NIST MS number 227588

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Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySE-30130.575.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySE-3080.575.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySqualane50.562.8Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.562.7Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane50.562.8Bajus, Veselý, et al., 1979, 2Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.563.3Bajus, Veselý, et al., 1979, 2Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane100.560.7Lulova, Leont'eva, et al., 1976He; Column length: 120. m; Column diameter: 0.25 mm
CapillarySqualane50.563.Rijks and Cramers, 1974N2; Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.564.Rijks and Cramers, 1974N2; Column length: 100. m; Column diameter: 0.25 mm
PackedSqualane27.563.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.564.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.566.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.566.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane26.576.Zulaïca and Guiochon, 1966Column length: 10. m
PackedSqualane65.565.Adlard, Evans, et al., 1965Ar, Celite; Column length: 1.2 m
PackedSqualane78.567.Adlard, Evans, et al., 1965Ar, Celite; Column length: 1.2 m
PackedSqualane65.564.Adlard, Evans, et al., 1965Ar, Celite; Column length: 1.5 m
PackedSqualane78.563.Adlard, Evans, et al., 1965Ar, Celite; Column length: 1.5 m
PackedSqualane100.565.Adlard, Evans, et al., 1965N2, Celite; Column length: 1.8 m
PackedSqualane65.564.Adlard, Evans, et al., 1965N2, Celite; Column length: 1.8 m
PackedSqualane78.564.Adlard, Evans, et al., 1965N2, Celite; Column length: 1.8 m
PackedSqualane100.564.Adlard, Evans, et al., 1965Mixture, Celite; Column length: 1.5 m
PackedSqualane65.564.Adlard, Evans, et al., 1965Mixture, Celite; Column length: 1.5 m
PackedSqualane78.564.Adlard, Evans, et al., 1965Mixture, Celite; Column length: 1.5 m
PackedSqualane100.567.Adlard, Evans, et al., 1965He, Celite; Column length: 0.9 m
PackedSqualane65.566.Adlard, Evans, et al., 1965He, Celite; Column length: 0.9 m
PackedSqualane78.567.Adlard, Evans, et al., 1965He, Celite; Column length: 0.9 m
PackedSqualane100.565.Adlard, Evans, et al., 1965 
PackedSqualane65.565.Adlard, Evans, et al., 1965 
PackedSqualane78.565.Adlard, Evans, et al., 1965 

Kovats' RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryPetrocol DH-100581.6Haagen-Smit Laboratory, 1997He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min)

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryPetrocol DH568.Supelco, 2012100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min
CapillaryPetrocol DH578.Supelco, 2012100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.575.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, Notes

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

Fang and Rogers, 1992
Fang, W.; Rogers, D.W., Enthalpy of hydrogenation of the hexadienes and cis- and trans-1,3,5-hexatriene, J. Org. Chem., 1992, 57, 2294-2297. [all data]

Coops, Mulder, et al., 1946
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J., The heats of combustion of a number of hydrocarbons, Rec. Trav. Chim. Pays/Bas, 1946, 65, 128. [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]

Clopatt, 1932
Clopatt, J.A., Eine neue Methode zur Bestimmung der Verbrennungswarme fluchtiger Stoffe, Soc. Scient. Fenn. Commentat. Phys. Math., 1932, 6, 1-15. [all data]

Handrick, 1956
Handrick, G.R., Report of the study of pure explosive compounds. Part IV. Calculation of heat of combustion of organic compounds from structural features and calculation of power of high explosives, Rpt. C-58247 for the Office of the Chief of Ordnance, contract DA-19-020-ORD-47 by the Arthur D. Little, Inc., Cambridge, MA, 1956, 467-573. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [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]

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]

Bevan, Malkin, et al., 1955
Bevan, T.H.; Malkin, T.; Smith, D.B.; Davey, W.; Gwilt, J.R.; Cooper, W.; Kertes, S.; Roberts, J.J.; Ross, W.C.J.; Wilson, Walter; Cummings, G.A.McD.; McLaughlin, E., Notes, J. Chem. Soc., 1955, 1383, https://doi.org/10.1039/jr9550001383 . [all data]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [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]

Cummings and McLaughlin, 1955
Cummings, G.A.McD.; McLaughlin, E., Vapour Pressures of Some Unsaturated Hydrocarbons Containing Six Carbon Atoms, J. Chem. Soc., 1955, 1391-1392. [all data]

Molnar, Rachford, et al., 1984
Molnar, A.; Rachford, R.; Smith, G.V.; Liu, R., Heats of hydrogenation by a simple and rapid flow calorimetric method, Appl. Catal., 1984, 9, 219-223. [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
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]

Wolkoff, Holmes, et al., 1980
Wolkoff, P.; Holmes, J.L.; Lossing, F.P., On the formation of cyclopentenium cations from all C6H10+ molecular ion structures, Can. J. Chem., 1980, 58, 251. [all data]

Lossing and Traeger, 1975
Lossing, F.P.; Traeger, J.C., Stabilization in cyclopentadienyl, cyclopentenyl, and cyclopentyl cations, J. Am. Chem. Soc., 1975, 97, 1579. [all data]

Martin, Heller, et al., 1980
Martin, H.-D.; Heller, C.; Mayer, B.; Beckhaus, H.-D., Synthese bicyclischer, nicht-konjugierter Polyene. Stereochemie und transanulare Wechselwirkungen, Chem. Ber., 1980, 113, 2589. [all data]

Bunzli, Burak, et al., 1973
Bunzli, J.C.; Burak, A.J.; Frost, D.C., Through-space interaction in non-conjugated acyclic dienes studied by photoelectron spectroscopy, Tetrahedron, 1973, 29, 3735. [all data]

Hart and Friedli, 1970
Hart, P.J.; Friedli, H.R., Desorption of allyl radicals in the heterogeneously-catalysed oxidation of propene: mass spectrometric study, Chem. Commun., 1970, 621. [all data]

Lossing and Traeger, 1975, 2
Lossing, F.P.; Traeger, J.C., Free radicals by mass spectrometry XLVI. Heats of formation of C5H7 and C5H9 radicals and cations., J. Am. Chem. Soc., 1975, 19, 9. [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

Bajus, Veselý, et al., 1979
Bajus, M.; Veselý, V.; Leclercq, P.A.; Rijks, J.A., Steam cracking of hydrocarbons. 2. Pyrolysis of methylcyclohexane, Ind. Eng. Chem. Prod. Res. Dev., 1979, 18, 2, 135-142, https://doi.org/10.1021/i360070a012 . [all data]

Bajus, Veselý, et al., 1979, 2
Bajus, M.; Veselý, V.; Leclercq, P.A.; Rijks, J.A., Steam cracking of hydrocarbons. 1. Pyrolysis of heptane, Ind. Eng. Chem. Prod. Res. Dev., 1979, 18, 1, 30-37, https://doi.org/10.1021/i360069a007 . [all data]

Lulova, Leont'eva, et al., 1976
Lulova, N.I.; Leont'eva, S.A.; Timofeeva, A.N., Gas-chromatographic method of determination of individual hydrocarbons in catalytic cracking gasolines in Proceedings of All-Union Research Institute on Oil Processes. Vol.18, All-Union Research Institute on Oil Processes, Moscow, 1976, 30-53. [all data]

Rijks and Cramers, 1974
Rijks, J.A.; Cramers, C.A., High precision capillary gas chromatography of hydrocarbons, Chromatographia, 1974, 7, 3, 99-106, https://doi.org/10.1007/BF02269819 . [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Zulaïca and Guiochon, 1966
Zulaïca, J.; Guiochon, G., Analyse des hauts polymères par chromatographie en phase gazeuse de leurs produits de pyrolyse. II. Application à quelques hydrocarbures macromoléculaires purs, Bull. Soc. Chim. Fr., 1966, 4, 1351-1363. [all data]

Adlard, Evans, et al., 1965
Adlard, E.R.; Evans, M.B.; Butlin, A.G.; Evans, R.S.; Hill, R.; Huber, J.F.K.; Littlewood, A.B.; McCambley, W.G.; Smith, J.F.; Swanton, W.T.; Swoboda, P.A.T., Recommendations of the data sub-committee for the publication of retention data, J. Gas Chromatogr., 1965, 3, 9, 298-302, https://doi.org/10.1093/chromsci/3.9.298 . [all data]

Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory, Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [all data]

Supelco, 2012
Supelco, CatalogNo. 24160-U, Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, References