2-Pentene, (Z)-
- Formula: C5H10
- Molecular weight: 70.1329
- 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 | -28. ± 4. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
98.8 | 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 |
99.3 | 300. | ||
128.3 | 400. | ||
155.6 | 500. | ||
179.4 | 600. | ||
199.2 | 700. | ||
216.5 | 800. | ||
231.4 | 900. | ||
244.3 | 1000. | ||
255.3 | 1100. | ||
265.0 | 1200. | ||
273.3 | 1300. | ||
280.6 | 1400. | ||
286.90 | 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 | -53.35 ± 0.42 | kJ/mol | Eqk | Wiberg, Wasserman, et al., 1984 | Trifluoroacetolysis, hrxn[kcal/mol]=-10.92±0.01; ALS |
ΔfH°liquid | -53.49 ± 0.62 | kJ/mol | Ccb | Good and Smith, 1979 | ALS |
ΔfH°liquid | -55.8 ± 1.0 | kJ/mol | Chyd | N/A | DRB |
ΔfH°liquid | -60.0 ± 0.3 | kJ/mol | Cm | Coops, Mulder, et al., 1946 | DRB |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3343.21 ± 0.54 | kJ/mol | Ccb | Good and Smith, 1979 | Corresponding ΔfHºliquid = -53.49 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -3336.7 ± 0.3 | kJ/mol | Cm | Coops, Mulder, et al., 1946 | Reanalyzed by Cox and Pilcher, 1970, Original value = -3335.3 ± 0.3 kJ/mol; Corresponding ΔfHºliquid = -60.04 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 258.8 | J/mol*K | N/A | Chao, Hall, et al., 1983 | DH |
S°liquid | 258.61 | J/mol*K | N/A | Todd, Oliver, et al., 1947 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
151.8 | 298.15 | Chao, Hall, et al., 1983 | T = 13 to 295 K.; DH |
151.71 | 298.15 | Todd, Oliver, et al., 1947 | T = 12 to 300 K.; DH |
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 | 309.8 ± 0.6 | K | AVG | N/A | Average of 23 out of 25 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 120.67 | K | N/A | Hoff, Greenlee, et al., 1951 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 121.77 | K | N/A | Hoff, Greenlee, et al., 1951 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 120.59 | K | N/A | Hoff, Greenlee, et al., 1951 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 121.74 | K | N/A | Streiff, Murphy, et al., 1946 | Uncertainty assigned by TRC = 0.05 K; TRC |
Tfus | 121.78 | K | N/A | Streiff, Murphy, et al., 1946 | Uncertainty assigned by TRC = 0.04 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 121.78 | K | N/A | Chao, Hall, et al., 1983, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 121.80 | K | N/A | Todd, Oliver, et al., 1947, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 475. ± 1. | K | N/A | Tsonopoulos and Ambrose, 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 36.9 ± 1.0 | bar | N/A | Tsonopoulos and Ambrose, 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 26.8 | kJ/mol | N/A | Reid, 1972 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
29.8 | 249. | A | Stephenson and Malanowski, 1987 | Based on data from 234. to 318. K.; AC |
28.1 | 289. | EB | Scott and Waddington, 1950 | Based on data from 274. to 341. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
274.74 to 342.03 | 3.99984 | 1069.229 | -42.393 | Scott and Waddington, 1950 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.112 | 121.78 | Chao, Hall, et al., 1983 | DH |
7.1115 | 121.80 | Todd, Oliver, et al., 1947 | DH |
7.11 | 121.8 | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
58.40 | 121.78 | Chao, Hall, et al., 1983 | DH |
58.39 | 121.80 | Todd, Oliver, et al., 1947 | 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° | -4.90 ± 0.08 | kJ/mol | Eqk | Kapteijn, Steen, et al., 1983 | gas phase; Between 250-823 K |
ΔrH° | -4. ± 0.63 | kJ/mol | Eqk | Egger and Benson, 1966 | gas phase; Heat of isomerization |
By formula: H2 + C5H10 = C5H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -117.7 ± 0.8 | kJ/mol | Chyd | Egger and Benson, 1966 | gas phase |
By formula: C5H11Cl = C5H10 + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 65.3 | kJ/mol | Eqk | Karaseva and Andreevskii, 1969 | gas phase |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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
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, Phase change 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]
Hoff, Greenlee, et al., 1951
Hoff, M.C.; Greenlee, K.W.; Boord, C.E.,
The Quantitavitve Inversion of cis- and trans-Alkene Isomers: A New Synthesis of Normal cis-Alkenes,
J. Am. Chem. Soc., 1951, 73, 3329-36. [all data]
Streiff, Murphy, et al., 1946
Streiff, A.J.; Murphy, E.T.; Sedlak, V.A.; Willingham, C.B.; Rossini, F.D.,
Purification, Purity, and Freezing Points of 7 Heptanes, 16 Octanes, 6 Pentene, Cyclopentene, and 7 C9H12 Alkylbenzenes of the API-Standard and API-NBS Series,
J. Res. Natl. Bur. Stand. (U. S.), 1946, 37, 331. [all data]
Chao, Hall, et al., 1983, 2
Chao, J.; Hall, K.R.; Yao, J.M.,
Thermodynamic Properties of Simple Alkenes,
Thermochim. Acta, 1983, 64, 285. [all data]
Todd, Oliver, et al., 1947, 2
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. [all data]
Tsonopoulos and Ambrose, 1996
Tsonopoulos, C.; Ambrose, D.,
Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons,
J. Chem. Eng. Data, 1996, 41, 645-656. [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]
Scott and Waddington, 1950
Scott, Donald W.; Waddington, Guy,
Vapor Pressure of cis-2-Pentene, trans-2-Pentene and 3-Methyl-1-butene,
J. Am. Chem. Soc., 1950, 72, 9, 4310-4311, https://doi.org/10.1021/ja01165a542
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [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, Phase change 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 Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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