2-Pentene, (Z)-
- Formula: C5H10
- Molecular weight: 70.1329
- IUPAC Standard InChI: InChI=1S/C5H10/c1-3-5-4-2/h3,5H,4H2,1-2H3/b5-3-
- IUPAC Standard InChIKey: QMMOXUPEWRXHJS-HYXAFXHYSA-N
- CAS Registry Number: 627-20-3
- 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)-2-Pentene; cis-β-Amylene; cis-Pentene; cis-2-Pentene; 2-(Z)-C5H10; cis-Pentene-2; Pentene-2, cis-; (Z)-pent-2-ene
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Gas 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
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 | -7. ± 1. | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 23.6 | 298.15 | Thermodynamics Research Center, 1997 | p=1 bar. Recommended values were calculated from data for lower alkenes by a method of increments. These values are in good agreement with experimental data (see also [ Kilpatrick J.E., 1946]).; GT |
| 23.7 | 300. | ||
| 30.66 | 400. | ||
| 37.19 | 500. | ||
| 42.88 | 600. | ||
| 47.61 | 700. | ||
| 51.74 | 800. | ||
| 55.31 | 900. | ||
| 58.39 | 1000. | ||
| 61.02 | 1100. | ||
| 63.34 | 1200. | ||
| 65.32 | 1300. | ||
| 67.07 | 1400. | ||
| 68.571 | 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -12.75 ± 0.10 | kcal/mol | Eqk | Wiberg, Wasserman, et al., 1984 | Trifluoroacetolysis, hrxn[kcal/mol]=-10.92±0.01; ALS |
| ΔfH°liquid | -12.78 ± 0.15 | kcal/mol | Ccb | Good and Smith, 1979 | ALS |
| ΔfH°liquid | -13.3 ± 0.24 | kcal/mol | Chyd | N/A | DRB |
| ΔfH°liquid | -14.3 ± 0.07 | kcal/mol | Cm | Coops, Mulder, et al., 1946 | DRB |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -799.05 ± 0.13 | kcal/mol | Ccb | Good and Smith, 1979 | Corresponding ΔfHºliquid = -12.78 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -797.48 ± 0.07 | kcal/mol | Cm | Coops, Mulder, et al., 1946 | Reanalyzed by Cox and Pilcher, 1970, Original value = -797.16 ± 0.07 kcal/mol; Corresponding ΔfHºliquid = -14.35 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 61.85 | cal/mol*K | N/A | Chao, Hall, et al., 1983 | DH |
| S°liquid | 61.809 | cal/mol*K | N/A | Todd, Oliver, et al., 1947 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 36.28 | 298.15 | Chao, Hall, et al., 1983 | T = 13 to 295 K.; DH |
| 36.260 | 298.15 | Todd, Oliver, et al., 1947 | T = 12 to 300 K.; 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 by: 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
=
By formula: C5H10 = C5H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.17 ± 0.02 | kcal/mol | Eqk | Kapteijn, Steen, et al., 1983 | gas phase; Between 250-823 K |
| ΔrH° | -0.9 ± 0.15 | kcal/mol | Eqk | Egger and Benson, 1966 | gas phase; Heat of isomerization |
+
=
By formula: H2 + C5H10 = C5H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -28.1 ± 0.2 | kcal/mol | Chyd | Egger and Benson, 1966 | gas phase |
=
+
By formula: C5H11Cl = C5H10 + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.6 | kcal/mol | Eqk | Karaseva and Andreevskii, 1969 | gas phase |
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:
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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
View reactions leading to C5H10+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 9.01 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.94 ± 0.02 | PE | Ashmore and Burgess, 1978 | LLK |
| 9.04 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
| 9.036 ± 0.005 | PE | Masclet, Grosjean, et al., 1973 | LLK |
| 9.23 ± 0.02 | EI | Gross and Wilkins, 1971 | LLK |
| 9.11 | EI | Collin and Lossing, 1959 | RDSH |
| 9.22 ± 0.01 | PE | Krause, Taylor, et al., 1978 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C3H6+ | 11.54 ± 0.02 | C2H4 | EI | Gross and Wilkins, 1971 | LLK |
| C4H7+ | 9.02 | CH3 | PI | Traeger, 1986 | LBLHLM |
| C4H7+ | 10.62 | CH3 | PI | Traeger, 1986 | LBLHLM |
| C4H7+ | 11.24 ± 0.02 | CH3 | EI | Gross and Wilkins, 1971 | LLK |
References
Go To: Top, Gas phase thermochemistry data, 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.
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]
Kilpatrick J.E., 1946
Kilpatrick J.E.,
Heats, equilibrium constants, and free energies of formation of the monoolefin hydrocarbons,
J. Res. Nat. Bur. Stand, 1946, 36, 559-612. [all data]
Wiberg, Wasserman, et al., 1984
Wiberg, K.B.; Wasserman, D.J.; Martin, E.,
Enthalpies of hydration of alkenes. 2. The n-heptenes and n-pentenes,
J. Phys. Chem., 1984, 88, 3684-3688. [all data]
Good and Smith, 1979
Good, W.D.; Smith, N.K.,
The enthalpies of combustion of the isomeric pentenes in the liquid state. A warning to combustion calorimetrists about sample drying,
J. Chem. Thermodyn., 1979, 11, 111-118. [all data]
Coops, Mulder, et al., 1946
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J.,
The heats of combustion of a number of hydrocarbons,
Rec. Trav. Chim. Pays/Bas, 1946, 65, 128. [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]
Chao, Hall, et al., 1983
Chao, J.; Hall, K.R.; Yao, J.M.,
Thermodynamic properties of simple alkenes,
Thermochim. Acta, 1983, 64(3), 285-303. [all data]
Todd, Oliver, et al., 1947
Todd, S.S.; Oliver, G.D.; Huffman, H.M.,
The heat capacities, heats of fusion and entropies of the six pentenes,
J. Am. Chem. Soc., 1947, 69, 1519-1525. [all data]
Kapteijn, Steen, et al., 1983
Kapteijn, F.; Steen, A.J.; Mol, J.C.,
Thermodynamics of the geometrical isomerization of 2-butene and 2-pentene,
J. Chem. Thermodyn., 1983, 15, 137-146. [all data]
Egger and Benson, 1966
Egger, K.W.; Benson, S.W.,
Nitric oxide and iodine catalyzed isomerization of olefins. VI. Thermodynamic data from equilibrium studies of the geometrical and positional isomerization of n-pentenes,
J. Am. Chem. Soc., 1966, 88, 236-240. [all data]
Karaseva and Andreevskii, 1969
Karaseva, S.Ya.; Andreevskii, D.N.,
Equilibrium in the isomerisation of secondary monochloropentanes and the dehydrochlorination of 2-chloropentane,
Russ. J. Phys. Chem. (Engl. Transl.), 1969, 43, 1236-1238. [all data]
Ashmore and Burgess, 1978
Ashmore, F.S.; Burgess, A.R.,
Photoelectron spectra of the unbranched C5-C7 alkenes, aldehydes and ketones,
J. Chem. Soc. Faraday Trans. 2, 1978, 74, 734. [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]
Masclet, Grosjean, et al., 1973
Masclet, P.; Grosjean, D.; Mouvier, G.,
Alkene ionization potentials. Part I. Quantitative determination of alkyl group structural effects,
J. Electron Spectrosc. Relat. Phenom., 1973, 2, 225. [all data]
Gross and Wilkins, 1971
Gross, M.L.; Wilkins, C.L.,
Computer-assisted ion cyclotron resonance appearance potential measurements for C5H10 isomers,
Anal. Chem., 1971, 43, 1624. [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]
Krause, Taylor, et al., 1978
Krause, D.A.; Taylor, J.W.; Fenske, R.F.,
An analysis of the effects of alkyl substituents on the ionization potentials of n-alkenes,
J. Am. Chem. Soc., 1978, 100, 718. [all data]
Traeger, 1986
Traeger, J.C.,
Heat of formation for the 1-methylallyl cation by photoionization mass spectrometry,
J. Phys. Chem., 1986, 90, 4114. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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 IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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