1,2-Pentadiene
- Formula: C5H8
- Molecular weight: 68.1170
- IUPAC Standard InChIKey: LVMTVPFRTKXRPH-UHFFFAOYSA-N
- CAS Registry Number: 591-95-7
- 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. - Other names: Ethylallene; 1-Methyl-2,3-butadiene; CH2=C=CHCH2CH3; penta-1,2-diene
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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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:
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 |
---|---|---|---|---|---|
Tboil | 318.1 | K | N/A | Anonymous, 1959 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tboil | 319. | K | N/A | Jacobs, Akawie, et al., 1951 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 318. | K | N/A | Bouis, 1928 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 135.880 | K | N/A | Anonymous, 1959 | Uncertainty assigned by TRC = 0.03 K; TRC |
Tfus | 135.870 | K | N/A | Anonymous, 1959 | Uncertainty assigned by TRC = 0.04 K; TRC |
Tfus | 135.890 | K | N/A | Anonymous, 1959 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 135.840 | K | N/A | Streiff, Soule, et al., 1950 | Uncertainty assigned by TRC = 0.03 K; TRC |
Tfus | 135.820 | K | N/A | Streiff, Soule, et al., 1950 | Uncertainty assigned by TRC = 0.04 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 135.89 | K | N/A | Messerly, Todd, et al., 1970 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 6.86 | kcal/mol | N/A | Reid, 1972 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.55 | 240. | A | Stephenson and Malanowski, 1987 | Based on data from 231. to 249. K.; AC |
7.31 | 264. | A | Stephenson and Malanowski, 1987 | Based on data from 249. to 331. K.; AC |
7.70 | 231. | IP | Osborn and Douslin, 1969 | Based on data from 213. to 245. K.; AC |
6.96 | 300. | MM | Forziati, Camin, et al., 1950 | Based on data from 285. to 319. 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 244.66 | 4.05551 | 1125.536 | -41.27 | Osborn and Douslin, 1969 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.8067 | 135.89 | Messerly, Todd, et al., 1970, 2 | DH |
1.81 | 135.9 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.295 | 135.89 | Messerly, Todd, et al., 1970, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, 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:
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)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.25 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.42 | EI | Collin and Lossing, 1959 | RDSH |
9.22 | PE | Kroner, Kosbahn, et al., 1977 | Vertical value; LLK |
Gas Chromatography
Go To: Top, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-1 | 27. | 526. | Heberger, 1990 | 25. m/0.25 mm/0.50 μm, He |
Capillary | Squalane | 50. | 525. | Bajus, Veselý, et al., 1979 | Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 70. | 526. | Bajus, Veselý, et al., 1979 | 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. | 526. | Rijks and Cramers, 1974 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Packed | Squalane | 27. | 526. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 527. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 527. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 527. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 26. | 527. | Zulaïca and Guiochon, 1966 | Column length: 10. m |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Anonymous, 1959
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 6, Carnegie-Mellon Univ., 1959. [all data]
Jacobs, Akawie, et al., 1951
Jacobs; Akawie; Copper,
Rearrangements Involving 1-Pentyne, 2-Pentyne and 1,2-Pentadiene,
J. Am. Chem. Soc., 1951, 73, 1273. [all data]
Bouis, 1928
Bouis, M.,
Ann. Chim. (Paris), 1928, 9, 402. [all data]
Streiff, Soule, et al., 1950
Streiff, A.J.; Soule, L.F.; Kennedy, C.M.; Janes, M.E.; Sedlak, V.A.; Willingham, C.B.; Rossini, F.D.,
Purification, purity, and freezing points of twenty-nine hydrocarbons of the API-standard and API-NBS series.,
J. Res. Natl. Bur. Stand. (U. S.), 1950, 45, 173. [all data]
Messerly, Todd, et al., 1970
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]
Messerly, Todd, et al., 1970, 2
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]
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]
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]
Collin and Lossing, 1959
Collin, J.; Lossing, F.P.,
Ionization potentials of some olefins, di-olefins and branched paraffins,
J. Am. Chem. Soc., 1959, 81, 2064. [all data]
Kroner, Kosbahn, et al., 1977
Kroner, J.; Kosbahn, W.; Runge, W.,
The molecular structure of allenes and ketenes, IX[1]π and σ interactions in allenes: Photoelectron spectra, electronic absorption spectra, and quantum chemical calculations,
Ber. Bunsen-Ges. Phys. Chem., 1977, 81, 826. [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]
Bajus, Veselý, et al., 1979
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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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