1,3-Pentadiene, (E)-

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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 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
ΔfH°gas18.11 ± 0.16kcal/molCmFraser and Prosen, 1955ALS
Quantity Value Units Method Reference Comment
ΔcH°gas-761.64 ± 0.15kcal/molCmFraser and Prosen, 1955Corresponding ΔfHºgas = 18.12 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
S°gas75.430cal/mol*KN/AMesserly J.F., 1970GT

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
8.83450.Thermodynamics Research Center, 1997Comparison with other statistical thermodynamics calculations [ Petrova-Kuminskaya S.V., 1986, Compton D.A.C., 1977] show that S and Cp values from TRC Tables are possibly underestimated at high temperatures.; GT
12.08100.
15.03150.
17.82200.
22.13273.15
23.68298.15
23.79300.
29.897400.
35.368500.
40.017600.
43.956700.
47.32800.
50.22900.
52.721000.
54.881100.
56.741200.
58.371300.
59.781400.
60.991500.

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 by: Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
S°liquid54.281cal/mol*KN/AMesserly, Todd, et al., 1970 

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
35.691298.15Messerly, Todd, et al., 1970T = 12 to 320 K.

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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil315.1 ± 0.4KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus185.2 ± 0.9KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple185.71KN/AMesserly, Todd, et al., 1970, 2Uncertainty assigned by TRC = 0.05 K; TRC
Quantity Value Units Method Reference Comment
ΔvapH°6.64kcal/molN/AReid, 1972AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
7.34242.AStephenson and Malanowski, 1987Based on data from 228. to 256. K.; AC
7.05271.AStephenson and Malanowski, 1987Based on data from 256. to 324. K.; AC
7.48230.IPOsborn and Douslin, 1969Based on data from 213. to 242. K.; AC
6.76304.MMForziati, Camin, et al., 1950Based on data from 292. to 316. 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
213.14 to 242.224.247711196.308-32.775Osborn and Douslin, 1969Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
1.7074185.71Messerly, Todd, et al., 1970DH
1.71185.7Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
9.1941185.71Messerly, Todd, et al., 1970DH

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

C5H7- + Hydrogen cation = 1,3-Pentadiene, (E)-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
ΔrH°369.2 ± 1.2kcal/molD-EAZimmerman, Gygax, et al., 1978gas phase; Acid: 1,4-pentadiene. (Z)-1,3-pentadiene is 7.0 kcal/mol more stable(weaker acid); B
Quantity Value Units Method Reference Comment
ΔrG°364.4 ± 1.9kcal/molH-TSZimmerman, Gygax, et al., 1978gas phase; Acid: 1,4-pentadiene. (Z)-1,3-pentadiene is 7.0 kcal/mol more stable(weaker acid); B

1,3-Pentadiene, (Z)- = 1,3-Pentadiene, (E)-

By formula: C5H8 = C5H8

Quantity Value Units Method Reference Comment
ΔrH°-1.01 ± 0.18kcal/molEqkEgger and Benson, 1965gas phase; Heat of isomerization; ALS

Chlorine anion + 1,3-Pentadiene, (E)- = (Chlorine anion • 1,3-Pentadiene, (E)-)

By formula: Cl- + C5H8 = (Cl- • C5H8)

Quantity Value Units Method Reference Comment
ΔrG°3.70kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

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
CapillaryOV-127.515.Heberger, 199025. m/0.25 mm/0.50 μm, He
CapillaryOV-130.526.Heberger, 199025. m/0.25 mm/0.50 μm, He
CapillaryOV-140.506.Heberger, 199025. m/0.25 mm/0.50 μm, He
CapillaryOV-175.522.Heberger, 199025. m/0.25 mm/0.50 μm, He
PackedSqualane70.516.Safina, Poznyak, et al., 1989He, Risorb (0.2-0.3 mm); Column length: 2. m
CapillarySqualane50.515.8Papazova, Milina, et al., 1988Column length: 50. m; Column diameter: 0.25 mm
CapillarySqualane50.515.700Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.516.5Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane50.515.700Bajus, Veselý, et al., 1979, 2Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.516.2Bajus, Veselý, et al., 1979, 2Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane50.526.Rijks and Cramers, 1974N2; Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.516.Rijks and Cramers, 1974N2; Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane27.513.75Schomburg and Dielmann, 1973Column length: 100. m; Column diameter: 0.25 mm
PackedSqualane27.515.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.516.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.518.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.519.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane26.518.Zulaïca and Guiochon, 1966Column length: 10. m

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

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Column type Active phase I Reference Comment
CapillaryPetrocol DH-100528.Haagen-Smit Laboratory, 1997He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min)
CapillaryDB-1526.Hoekman, 199360. m/0.32 mm/1.0 μm, He; Program: -40 C for 12 min; -40 - 125 C at 3 deg.min; 125-185 C at 6 deg/min; 185 - 220 C at 20 deg/min; hold 220 C for 2 min

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryDB-1524.Kaiser and Siegl, 199460. m/0.32 mm/1. μm, -50. C @ 4. min, 6. K/min; Tend: 180. C

Normal alkane RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySqualane70.515.Schomburg, 1966 

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane: CP-Sil 5 CB521.Bramston-Cook, 201360. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min
CapillaryPetrocol DH523.Supelco, 2012100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min
CapillaryHP-1519.Berlioz, Cordella, et al., 200650. m/0.2 mm/0.33 μm, N2, 2. K/min, 250. C @ 20. min; Tstart: 60. C
CapillaryOV-101521.Chupalov and Zenkevich, 1996N2, 3. K/min; Column length: 52. m; Column diameter: 0.26 mm; Tstart: 50. C; Tend: 220. C

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

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Column type Active phase I Reference Comment
CapillaryPONA528.Perkin Elmer Instruments, 2002Column length: 100. m; Phase thickness: 0.50 μm; Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, Notes

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

Fraser and Prosen, 1955
Fraser, F.M.; Prosen, E.J., Heats of combustion and isomerization of six pentadienes and spiropentane, J. Res. NBS, 1955, 54, 143-148. [all data]

Messerly J.F., 1970
Messerly J.F., Chemical thermodynamic properties of the pentadienes. Third law studies, J. Chem. Eng. Data, 1970, 15, 227-232. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Petrova-Kuminskaya S.V., 1986
Petrova-Kuminskaya S.V., Thermodynamic properties of 1,4-pentadiene and trans-1,3-pentadiene calculated by statistical thermodynamics method, Vestn. Beloruss. Univ., Ser. 2, 1986, 6-8. [all data]

Compton D.A.C., 1977
Compton D.A.C., Conformations of conjugated hydrocarbons. Part 2. A spectroscopic and thermodynamic study of cis- and trans-penta-1,3-diene, J. Chem. Soc. Perkin Trans. 2, 1977, 1311-1315. [all data]

Messerly, Todd, et al., 1970
Messerly, J.F.; Todd, S.S.; Guthrie, G.B., Chemical thermodynamic properties of the pentadienes, J. Chem. Eng. Data, 1970, 15, 227-232. [all data]

Messerly, Todd, et al., 1970, 2
Messerly, J.F.; Todd, S.S.; Guthrie, G.B., Chemical thermodynamic properties of the pentadienes. Third law studies., J. Chem. Eng. Data, 1970, 15, 227-32. [all data]

Reid, 1972
Reid, Robert C., Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00, AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637 . [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]

Osborn and Douslin, 1969
Osborn, Ann G.; Douslin, Donald R., Vapor pressure relations for the seven pentadienes, J. Chem. Eng. Data, 1969, 14, 2, 208-209, https://doi.org/10.1021/je60041a010 . [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]

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]

Zimmerman, Gygax, et al., 1978
Zimmerman, A.H.; Gygax, R.; Brauman, J.I., Electron photodetachment spectroscopy of polyene anions. Electron affinities of pentadienyl and heptatrienyl radicals, J. Am. Chem. Soc., 1978, 100, 5595. [all data]

Egger and Benson, 1965
Egger, K.W.; Benson, S.W., Nitric oxide and iodine catalyzed isomerization of olefins. IV. Thermodynamic data from equilibrium studies of the geometrical isomerization of 1,3-pentadiene, J. Am. Chem. Soc., 1965, 87, 3311-3314. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-, Can. J. Chem., 1982, 60, 1907. [all data]

Heberger, 1990
Heberger, K., Identification of C5H8 Isomers Through Reactions of Singlet Methylene, CH2(ã1A1), with Unsaturated Hydrocarbons Using Capillary Gas Chromatography - Mass Spectrometry, Analyst, 1990, 115, 6, 725-729, https://doi.org/10.1039/an9901500725 . [all data]

Safina, Poznyak, et al., 1989
Safina, L.R.; Poznyak, T.I.; Lisitsyn, D.M.; Kiseleva, E.V.; Kovalev, G.I., Selective gas-chromatographic determination of trace unsaturated and aromatic-hydrocarbons in complex-mixtures, J. Appl. Chem. USSR (Engl. Transl.), 1989, 44, 5, 749-754. [all data]

Papazova, Milina, et al., 1988
Papazova, D.; Milina, R.; Dimov, N., Comparative evaluation of retention of hydrocarbons present in the C5-petroleum fraction of methylsilicone and squalane phases, Chromatographia, 1988, 25, 3, 177-180, https://doi.org/10.1007/BF02316441 . [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]

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]

Schomburg and Dielmann, 1973
Schomburg, G.; Dielmann, G., Identification by means of retention parameters, J. Chromatogr. Sci., 1973, 11, 3, 151-159, https://doi.org/10.1093/chromsci/11.3.151 . [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]

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]

Hoekman, 1993
Hoekman, S.K., Improved gas chromatography procedure for speciated hydrocarbon measurements of vehicle emissions, J. Chromatogr., 1993, 639, 2, 239-253, https://doi.org/10.1016/0021-9673(93)80260-F . [all data]

Kaiser and Siegl, 1994
Kaiser, E.W.; Siegl, W.O., High resolution gas chromatographic determination of the atmospheric reactivity of engine-out hydrocarbon emissions from a spark-ignited engine, J. Hi. Res. Chromatogr., 1994, 17, 4, 264-270, https://doi.org/10.1002/jhrc.1240170414 . [all data]

Schomburg, 1966
Schomburg, G., Gaschromatographische Retentionsdaten und Struktur Chemischer Verbindungen. II. Methylverzweigungen und Doppelbindungen in Offenkettigen Kohlenwasserstoffen, J. Chromatogr., 1966, 23, 1-17, https://doi.org/10.1016/S0021-9673(01)98652-2 . [all data]

Bramston-Cook, 2013
Bramston-Cook, R., Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [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]

Berlioz, Cordella, et al., 2006
Berlioz, B.; Cordella, C.; Cavalli, J.-F.; Lizzani-Cuvelier, L.; Loiseau, A.-M.; Fernandez, X., Comparison of the amounts of volatile compounds in French protected designation of origin virgin olive oils, J. Agric. Food Chem., 2006, 54, 26, 10092-10101, https://doi.org/10.1021/jf061796+ . [all data]

Chupalov and Zenkevich, 1996
Chupalov, A.A.; Zenkevich, I.G., Chromatographic Characterization of Structural Transformations of Organic Compounds in Diels-Alder Reaction. Aliphatic Dienes and Dienophyls, Zh. Org. Khim., 1996, 32, 6, 675-684. [all data]

Perkin Elmer Instruments, 2002
Perkin Elmer Instruments, Detailed hydrocarbon analysis (DHAX) Model 4015, 2002, retrieved from http://www.perkinelmer.com/instruments. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References