1,3-Pentadiene, (Z)-
- 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-PLNGDYQASA-N
- CAS Registry Number: 1574-41-0
- 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: (Z)-1,3-Pentadiene; cis-Piperylene; cis-1-Methylbutadiene; cis-1,3-Pentadiene; (Z)-CH2=CHCH=CHCH3; 1,cis-3-Pentadiene; Pentadiene-1,3, cis-; (Z)-penta-1,3-diene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References, Notes
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°gas | 19.77 ± 0.22 | kcal/mol | Cm | Fraser and Prosen, 1955 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°gas | -763.30 ± 0.21 | kcal/mol | Cm | Fraser and Prosen, 1955 | Corresponding ΔfHºgas = 19.78 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 77.151 | cal/mol*K | N/A | Messerly J.F., 1970 | GT |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 10.06 | 50. | Thermodynamics Research Center, 1997 | Entropy values from other statistical thermodynamics calculation [ Compton D.A.C., 1977] are substantially lower (up to 14 J/mol*K) than recommended ones and experimental value of S(298.15 K). Discrepancies in Cp(T) values do not exceed 2.5 J/mol*K. Values of thermodynamic functions calculated from data for lower alkenes and alkadienes by a method of increments [ Kilpatrick J.E., 1949] agree with TRC values within 1-3 J/mol*K.; GT |
| 13.03 | 100. | ||
| 15.21 | 150. | ||
| 17.57 | 200. | ||
| 21.69 | 273.15 | ||
| 23.23 | 298.15 | ||
| 23.34 | 300. | ||
| 29.496 | 400. | ||
| 35.043 | 500. | ||
| 39.763 | 600. | ||
| 43.762 | 700. | ||
| 47.18 | 800. | ||
| 50.12 | 900. | ||
| 52.63 | 1000. | ||
| 54.83 | 1100. | ||
| 56.72 | 1200. | ||
| 58.34 | 1300. | ||
| 59.78 | 1400. | ||
| 60.99 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
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 | 55.748 | cal/mol*K | N/A | Messerly, Todd, et al., 1970 |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 35.031 | 298.15 | Messerly, Todd, et al., 1970 | T = 12 to 320 K. |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes
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 C5H8+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 8.62 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.64 | PE | Rucker, Lang, et al., 1980 | LLK |
| 8.67 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
| 8.59 | PE | Dewar and Worley, 1968 | RDSH |
| 8.63 | PE | Masclet, Mouvier, et al., 1981 | Vertical value; LLK |
| 8.60 | PE | Worley, Webb, et al., 1980 | Vertical value; LLK |
| 8.60 | PE | Worley, Webb, et al., 1979 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase 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.
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]
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]
Kilpatrick J.E., 1949
Kilpatrick J.E.,
Heats, equilibrium constants, and free energies of formation of the C3 to C5 diolefins, styrene, and the methylstyrenes,
J. Res. Nat. Bur. Stand., 1949, 42, 225-240. [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]
Rucker, Lang, et al., 1980
Rucker, C.; Lang, D.; Sauer, J.; Friege, H.; Sustmann, R.,
Reaktivitat substituierter 1,3-Butadiene in Diels-Alder-Reaktionen,
Chem. Ber., 1980, 113, 1663. [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]
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]
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]
Worley, Webb, et al., 1980
Worley, S.D.; Webb, T.R.; Gibson, D.H.; Ong, T.-S.,
The photoelectron spectra of some iron tricarbonyl complexes of 4π-electron donor ligands,
J. Electron Spectrosc. Relat. Phenom., 1980, 18, 189. [all data]
Worley, Webb, et al., 1979
Worley, S.D.; Webb, T.R.; Gibson, D.H.; Ong, T.-S.,
On the electronic structures of cyclobutadiene trimethylenemethane,
J. Organomet. Chem., 1979, 168, 16. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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