1,3-Pentadiene, (E)-

Formula: C₅H₈
Molecular weight: 68.1170
IUPAC Standard InChI: InChI=1S/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+
IUPAC Standard InChIKey: PMJHHCWVYXUKFD-SNAWJCMRSA-N
CAS Registry Number: 2004-70-8
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Stereoisomers:
- 1,3-Pentadiene, (Z)-
- 1,3-Pentadiene
Other names: (E)-1,3-Pentadiene; trans-Piperylene; trans-1-Methylbutadiene; trans-1,3-Pentadiene; (E)-CH2=CHCH=CHCH3; 1,trans-3-Pentadiene; Pentadiene-1,3,trans; trans-penta-1,3-diene
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Gas phase ion energetics data

Go To: Top, Gas Chromatography, References, Notes

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

View reactions leading to C₅H₈⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	8.59 ± 0.02	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	834.1	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	804.4	kJ/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.59 ± 0.02	PE	Masclet, Mouvier, et al., 1981	LLK
8.61 ± 0.02	PE	Bieri, Burger, et al., 1977	LLK
8.60	EI	Lossing and Traeger, 1975	LLK
8.61	PE	Beez, Bieri, et al., 1973	LLK
8.56	PE	Dewar and Worley, 1968	RDSH

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₃H₂⁺	20.9 ± 0.1	?	EI	Franklin and Mogenis, 1967	RDSH
C₃H₃⁺	15.16 ± 0.02	?	EI	Franklin and Mogenis, 1967	RDSH
C₃H₄⁺	12.63 ± 0.02	C₂H₄	EI	Franklin and Mogenis, 1967	RDSH
C₃H₅⁺	14.20 ± 0.02	?	EI	Franklin and Mogenis, 1967	RDSH
C₃H₆⁺	12.73 ± 0.03	C₂H₂	EI	Franklin and Mogenis, 1967	RDSH
C₄H₃⁺	16.36 ± 0.08	CH₃+H₂	EI	Franklin and Mogenis, 1967	RDSH
C₄H₄⁺	21.12 ± 0.08	?	EI	Franklin and Mogenis, 1967	RDSH
C₄H₅⁺	12.57 ± 0.05	CH₃	EI	Franklin and Mogenis, 1967	RDSH
C₄H₆⁺	13.1 ± 0.1	?	EI	Franklin and Mogenis, 1967	RDSH
C₅H₅⁺	13.90 ± 0.05	H₂+H	EI	Franklin and Mogenis, 1967	RDSH
C₅H₆⁺	12.34 ± 0.06	H₂	EI	Franklin and Mogenis, 1967	RDSH
C₅H₇⁺	8.60	H	EI	Lossing and Traeger, 1975, 2	LLK
C₅H₇⁺	10.52	H	EI	Lossing and Traeger, 1975	LLK
C₅H₇⁺	10.93 ± 0.02	H	EI	Franklin and Mogenis, 1967	RDSH

De-protonation reactions

C₅H₇^- + = 1,3-Pentadiene, (E)-

By formula: C₅H₇^- + H⁺ = C₅H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1545. ± 5.0	kJ/mol	D-EA	Zimmerman, Gygax, et al., 1978	gas 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
Δ_rG°	1525. ± 7.9	kJ/mol	H-TS	Zimmerman, Gygax, et al., 1978	gas phase; Acid: 1,4-pentadiene. (Z)-1,3-pentadiene is 7.0 kcal/mol more stable(weaker acid); B

Gas Chromatography

Go To: Top, Gas phase ion energetics data, References, Notes

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
Capillary	OV-1	27.	515.	Heberger, 1990	25. m/0.25 mm/0.50 μm, He
Capillary	OV-1	30.	526.	Heberger, 1990	25. m/0.25 mm/0.50 μm, He
Capillary	OV-1	40.	506.	Heberger, 1990	25. m/0.25 mm/0.50 μm, He
Capillary	OV-1	75.	522.	Heberger, 1990	25. m/0.25 mm/0.50 μm, He
Packed	Squalane	70.	516.	Safina, Poznyak, et al., 1989	He, Risorb (0.2-0.3 mm); Column length: 2. m
Capillary	Squalane	50.	515.8	Papazova, Milina, et al., 1988	Column length: 50. m; Column diameter: 0.25 mm
Capillary	Squalane	50.	515.700	Bajus, Veselý, et al., 1979	Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	70.	516.5	Bajus, Veselý, et al., 1979	Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	50.	515.700	Bajus, Veselý, et al., 1979, 2	Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	70.	516.2	Bajus, Veselý, et al., 1979, 2	Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	50.	526.	Rijks and Cramers, 1974	N2; Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	70.	516.	Rijks and Cramers, 1974	N2; Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	27.	513.75	Schomburg and Dielmann, 1973	Column length: 100. m; Column diameter: 0.25 mm
Packed	Squalane	27.	515.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	49.	516.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	67.	518.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	86.	519.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	26.	518.	Zulaïca and Guiochon, 1966	Column length: 10. m

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

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Column type	Active phase	I	Reference	Comment
Capillary	Petrocol DH-100	528.	Haagen-Smit Laboratory, 1997	He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min)
Capillary	DB-1	526.	Hoekman, 1993	60. 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
Capillary	DB-1	524.	Kaiser and Siegl, 1994	60. m/0.32 mm/1. μm, -50. C @ 4. min, 6. K/min; T_end: 180. C

Normal alkane RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	Squalane	70.	515.	Schomburg, 1966

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	Polydimethyl siloxane: CP-Sil 5 CB	521.	Bramston-Cook, 2013	60. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min
Capillary	Petrocol DH	523.	Supelco, 2012	100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min
Capillary	HP-1	519.	Berlioz, Cordella, et al., 2006	50. m/0.2 mm/0.33 μm, N2, 2. K/min, 250. C @ 20. min; T_start: 60. C
Capillary	OV-101	521.	Chupalov and Zenkevich, 1996	N2, 3. K/min; Column length: 52. m; Column diameter: 0.26 mm; T_start: 50. C; T_end: 220. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	PONA	528.	Perkin Elmer Instruments, 2002	Column length: 100. m; Phase thickness: 0.50 μm; Program: not specified

References

Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes

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]

Masclet, Mouvier, et al., 1981
Masclet, P.; Mouvier, G.; Bocquet, J.F., Effets electroniques et effets steriques dus a la substitution alcoyle dans les dienes conjugues, J. Chim. Phys., 1981, 78, 99. [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]

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]

Beez, Bieri, et al., 1973
Beez, M.; Bieri, G.; Bock, H.; Heilbronner, E., The ionization potentials of butadiene, hexatriene, andtheir methyl derivatives: evidence for through space interaction between double bond π-orbitals and non-bonded pseudo-π orbitals of methyl groups?, Helv. Chim. Acta, 1973, 56, 1028. [all data]

Dewar and Worley, 1968
Dewar, M.J.S.; Worley, S.D., Ionization potential of cis-1,3-butadiene, J. Chem. Phys., 1968, 49, 2454. [all data]

Franklin and Mogenis, 1967
Franklin, J.L.; Mogenis, A., An electron impact study of ions from several dienes, J. Phys. Chem., 1967, 71, 2820. [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]

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]

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 ion energetics data, Gas Chromatography, References

Symbols used in this document:

AE Appearance energy

IE (evaluated) Recommended ionization energy

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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AE	Appearance energy
IE (evaluated)	Recommended ionization energy
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions