1,3-Pentadiene, (E)-
- Formula: C5H8
- Molecular weight: 68.1170
- 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:
- 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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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°liquid | 227.11 | J/mol*K | N/A | Messerly, Todd, et al., 1970 |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
149.33 | 298.15 | Messerly, Todd, et al., 1970 | T = 12 to 320 K. |
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- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 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 |
ΔrG° | 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 |
By formula: C5H8 = C5H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.23 ± 0.75 | kJ/mol | Eqk | Egger and Benson, 1965 | gas phase; Heat of isomerization; ALS |
By formula: Cl- + C5H8 = (Cl- • C5H8)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 15.5 | kJ/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
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
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- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 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 |
ΔrG° | 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
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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