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 thermochemistry data

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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
Δ_fH°_gas	75.77 ± 0.67	kJ/mol	Cm	Fraser and Prosen, 1955	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-3186.7 ± 0.63	kJ/mol	Cm	Fraser and Prosen, 1955	Corresponding Δ_fHº_gas = 75.81 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_gas	315.60	J/mol*K	N/A	Messerly J.F., 1970	GT

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
36.96	50.	Thermodynamics Research Center, 1997	Comparison 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
50.54	100.
62.88	150.
74.55	200.
92.60	273.15
99.06	298.15
99.54	300.
125.09	400.
147.98	500.
167.43	600.
183.91	700.
198.0	800.
210.1	900.
220.6	1000.
229.6	1100.
237.4	1200.
244.2	1300.
250.1	1400.
255.2	1500.

Reaction thermochemistry data

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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^- + = 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

= 1,3-Pentadiene, (E)-

By formula: C₅H₈ = C₅H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-4.23 ± 0.75	kJ/mol	Eqk	Egger and Benson, 1965	gas phase; Heat of isomerization; ALS

+ 1,3-Pentadiene, (E)- = ( • )

By formula: Cl^- + C₅H₈ = (Cl^- • C₅H₈)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	15.5	kJ/mol	TDEq	French, Ikuta, et al., 1982	gas phase; B

Gas phase ion energetics data

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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

References

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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]

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]

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]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
IE (evaluated)	Recommended ionization energy
S°_gas	Entropy of gas at standard conditions
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
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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