1,4-Pentadiene
- Formula: C5H8
- Molecular weight: 68.1170
- IUPAC Standard InChIKey: QYZLKGVUSQXAMU-UHFFFAOYSA-N
- CAS Registry Number: 591-93-5
- 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: Penta-1,4-diene; CH2=CHCH2CH=CH2; Pentadiene-1,4
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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 | 25.41 ± 0.31 | kcal/mol | Cm | Fraser and Prosen, 1955 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -768.94 ± 0.30 | kcal/mol | Cm | Fraser and Prosen, 1955 | Corresponding ΔfHºgas = 25.42 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 79.821 | 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 |
---|---|---|---|
10.29 | 50. | Thermodynamics Research Center, 1997 | Maximum discrepancies with other statistically calculated values [ Petrova-Kuminskaya S.V., 1986] amount to about 6 and 11 J/mol*K for S(1000 K) and Cp(298.15 K).; GT |
12.79 | 100. | ||
14.87 | 150. | ||
17.39 | 200. | ||
21.84 | 273.15 | ||
23.48 | 298.15 | ||
23.60 | 300. | ||
30.093 | 400. | ||
35.834 | 500. | ||
40.655 | 600. | ||
44.692 | 700. | ||
48.16 | 800. | ||
51.08 | 900. | ||
53.61 | 1000. | ||
55.78 | 1100. | ||
57.70 | 1200. | ||
59.32 | 1300. | ||
60.76 | 1400. | ||
62.00 | 1500. |
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 | 59.479 | cal/mol*K | N/A | Messerly, Todd, et al., 1970 | |
S°liquid | 80.95 | cal/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 80 K, 47.11 J/mol*K. |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
35.091 | 298.15 | Messerly, Todd, et al., 1970 | T = 12 to 320 K. |
35.041 | 292.5 | Parks, Todd, et al., 1936 | T = 82 to 293 K. Value is unsmoothed experimental datum. |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
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 | 299. ± 2. | K | AVG | N/A | Average of 13 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 125.0 ± 0.3 | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 124.91 | K | N/A | Messerly, Todd, et al., 1970, 2 | Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 124.3 | K | N/A | Parks, Todd, et al., 1936, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 6.02 | kcal/mol | N/A | Reid, 1972 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.96 | 226. | A | Stephenson and Malanowski, 1987 | Based on data from 216. to 236. K.; AC |
6.72 | 251. | A | Stephenson and Malanowski, 1987 | Based on data from 236. to 307. K.; AC |
7.00 | 221. | IP | Osborn and Douslin, 1969 | Based on data from 213. to 230. K.; AC |
6.33 | 293. | MM | Forziati, Camin, et al., 1950 | Based on data from 288. to 300. K.; AC |
6.79 | 240. | N/A | Lamb and Roper, 1940 | Based on data from 194. to 255. 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 230.07 | 4.10416 | 1083.436 | -34.941 | Osborn and Douslin, 1969 | Coefficents calculated by NIST from author's data. |
194.31 to 291.23 | 4.15386 | 1108.225 | -32.104 | Lamb and Roper, 1940 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.4515 | 124.9 | Messerly, Todd, et al., 1970 | DH |
1.47 | 124.3 | Domalski and Hearing, 1996 | AC |
1.468 | 124.3 | Parks, Todd, et al., 1936 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.620 | 124.9 | Messerly, Todd, et al., 1970 | DH |
11.81 | 124.3 | Parks, Todd, et al., 1936 | DH |
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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
By formula: 2H2 + C5H8 = C5H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -60.22 ± 0.15 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -60.79 ± 0.15 kcal/mol; At 355 °K; ALS |
By formula: Cl- + C5H8 = (Cl- • C5H8)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
3.7 | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
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 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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
View reactions leading to C5H8+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.62 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.46 | EI | Lossing and Traeger, 1975 | LLK |
9.62 ± 0.02 | PE | Bunzli, Burak, et al., 1973 | LLK |
9.58 | EI | Collin and Lossing, 1959 | RDSH |
7.97 | PE | Martin, Heller, et al., 1980 | Vertical value; LLK |
9.72 | PE | Eaton and Traylor, 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H5+ | 11.04 | CH3 | EI | Lossing and Holmes, 1984 | LBLHLM |
C5H7+ | 9.46 | H | EI | Lossing and Traeger, 1975, 2 | LLK |
C5H7+ | 10.23 | H | EI | Lossing and Traeger, 1975 | LLK |
C5H7+ | 10.23 | H | EI | Holmes, 1974 | LLK |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: Cl- + C5H8 = (Cl- • C5H8)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
3.7 | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References, Notes
Data compiled by: Coblentz Society, Inc.
- GAS (100 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- LIQUID (100 mmHg DILUTED TO A TOTAL PRESSURE OF 600 mmHg WITH NITROGEN); DOW KBr FOREPRISM; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1340 CM-1, 10% IN CS2 FOR 1340-450 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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]
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]
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]
Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Shomate, C.H.,
Thermal data on organic compounds. XVII. Some heat capacity, entropy and free energy data for five higher olefins,
J. Am. Chem. Soc., 1936, 58, 2505-2508. [all data]
Messerly, Todd, et al., 1970, 2
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]
Parks, Todd, et al., 1936, 2
Parks, G.S.; Todd, S.S.; Shomate, C.H.,
Thermal data on organic compounds. XVII. Some heat capacity, entropy and free energy data for five higher olefins,
J. Am. Chem. Soc., 1936, 58, 2505. [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]
Lamb and Roper, 1940
Lamb, Arthur B.; Roper, Edwin E.,
The Vapor Pressures of Certain Unsaturated Hydrocarbons,
J. Am. Chem. Soc., 1940, 62, 4, 806-814, https://doi.org/10.1021/ja01861a032
. [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]
Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene,
J. Am. Chem. Soc., 1936, 58, 146-153. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
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]
Bunzli, Burak, et al., 1973
Bunzli, J.C.; Burak, A.J.; Frost, D.C.,
Through-space interaction in non-conjugated acyclic dienes studied by photoelectron spectroscopy,
Tetrahedron, 1973, 29, 3735. [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]
Martin, Heller, et al., 1980
Martin, H.-D.; Heller, C.; Mayer, B.; Beckhaus, H.-D.,
Synthese bicyclischer, nicht-konjugierter Polyene. Stereochemie und transanulare Wechselwirkungen,
Chem. Ber., 1980, 113, 2589. [all data]
Eaton and Traylor, 1974
Eaton, D.F.; Traylor, T.G.,
Distortional stabilization in phenyl participations,
J. Am. Chem. Soc., 1974, 96, 7109. [all data]
Lossing and Holmes, 1984
Lossing, F.P.; Holmes, J.L.,
Stabilization energy and ion size in carbocations in the gas phase,
J. Am. Chem. Soc., 1984, 106, 6917. [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]
Holmes, 1974
Holmes, J.L.,
The mass spectra of isomeric hydrocarbons - II: The C5H8 isomers, spiropentane, cyclopentene, 1,3-pentadiene and isoprene; the mechanisms and energetics of their fragmentations,
Org. Mass Spectrom., 1974, 8, 247. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions T Temperature Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions 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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