2-Butene, (Z)-
- Formula: C4H8
- Molecular weight: 56.1063
- IUPAC Standard InChIKey: IAQRGUVFOMOMEM-ARJAWSKDSA-N
- CAS Registry Number: 590-18-1
- 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-Butene; cis-Butene; cis-2-Butylene; cis-1,2-Dimethylethylene; cis-2-Butene; (Z)-2-C4H8; (2Z)-2-Butene; 2-Butene, cis-; Butene-2, cis-; 2-Butene, (2Z)-; (Z)-but-2-ene
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 | 220. | J/mol*K | N/A | Chao, Hall, et al., 1983 | |
S°liquid | 219.91 | J/mol*K | N/A | Scott, Ferguson, et al., 1944 | |
S°liquid | 212.88 | J/mol*K | N/A | Todd and Parks, 1936 | Extrapolation below 90 K, 48.95 J/mol*K. |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
127. | 298.15 | Chao, Hall, et al., 1983 | T = 5 to 367 K. |
130.00 | 299.8 | Schlinger and Sage, 1952 | T = 80 to 200°F. |
126.15 | 298.15 | Scott, Ferguson, et al., 1944 | T = 15 to 300 K. |
118.87 | 266.6 | Todd and Parks, 1936 | T = 93 to 267 K. Value is unsmoothed experimental datum. |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 276.84 ± 0.08 | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 133.85 | K | N/A | Kistiakowsky, Ruhoff, et al., 1935 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 134.26 | K | N/A | Chao, Hall, et al., 1983, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 134.26 | K | N/A | Scott, Ferguson, et al., 1944 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 133.8 | K | N/A | Todd and Parks, 1936, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 435.5 ± 0.1 | K | N/A | Tsonopoulos and Ambrose, 1996 | |
Tc | 435.6 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 435.55 | K | N/A | Ambrose, Cox, et al., 1960 | Uncertainty assigned by TRC = 0.3 K; Visual, PRT, IPTS-48; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 42.1 ± 0.5 | bar | N/A | Tsonopoulos and Ambrose, 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.2338 | l/mol | N/A | Tsonopoulos and Ambrose, 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 4.28 ± 0.05 | mol/l | N/A | Tsonopoulos and Ambrose, 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 22.7 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 22.1 | kJ/mol | N/A | Reid, 1972 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
23.34 | 276.9 | N/A | Majer and Svoboda, 1985 | |
24.4 | 275. | A | Stephenson and Malanowski, 1987 | Based on data from 221. to 290. K.; AC |
24.0 | 291. | A | Stephenson and Malanowski, 1987 | Based on data from 276. to 325. K.; AC |
23.6 | 339. | A | Stephenson and Malanowski, 1987 | Based on data from 324. to 386. K.; AC |
23.6 | 398. | A | Stephenson and Malanowski, 1987 | Based on data from 383. to 431. K.; AC |
22.5 | 246. | C | Scott, Ferguson, et al., 1944, 2 | AC |
22.47 | 246. | C | Scott, Ferguson, et al., 1944 | ALS |
24.31 | 276.73 | V | Kistiakowsky, Ruhoff, et al., 1935, 2 | At 355 °K; ALS |
25.3 | 252. | N/A | Hopkins, 1921 | Based on data from 195. to 267. K. See also Boublik, Fried, et al., 1984.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
246. to 292. | 36.37 | 0.2696 | 435.6 | Majer and Svoboda, 1985 |
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 |
---|---|---|---|---|---|
203.06 to 295.91 | 3.98744 | 957.06 | -36.504 | Scott, Ferguson, et al., 1944 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.309 | 134.26 | Chao, Hall, et al., 1983 | DH |
7.3092 | 134.26 | Scott, Ferguson, et al., 1944 | DH |
7.31 | 134.3 | Domalski and Hearing, 1996 | AC |
7.318 | 133.8 | Todd and Parks, 1936 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
54.4 | 134.26 | Chao, Hall, et al., 1983 | DH |
54.44 | 134.26 | Scott, Ferguson, et al., 1944 | DH |
54.69 | 133.8 | Todd and Parks, 1936 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C4H8+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.11 ± 0.01 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.13 | PI | Traeger, 1986 | LBLHLM |
9.13 | PI | Traeger, 1984 | LBLHLM |
9.11 ± 0.02 | PI | Wood and Taylor, 1979 | LLK |
9.108 ± 0.008 | EQ | Lias and Ausloos, 1978 | LLK |
9.12 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.124 ± 0.005 | PE | Masclet, Grosjean, et al., 1973 | LLK |
9.10 | EI | Lossing, 1972 | LLK |
9.07 | PE | Frost and Sandhu, 1971 | LLK |
9.119 | S | McDiarmid, 1969 | RDSH |
9.12 | PE | Dewar and Worley, 1969 | RDSH |
9.13 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.13 | PI | Bralsford, Harris, et al., 1960 | RDSH |
9.32 ± 0.01 | PE | Krause, Taylor, et al., 1978 | Vertical value; LLK |
9.20 | PE | Wiberg, Ellison, et al., 1976 | Vertical value; LLK |
9.11 ± 0.03 | PE | Heilbronner, Hoshi, et al., 1976 | Vertical value; LLK |
9.36 | PE | Kimura, Katsumata, et al., 1975 | Vertical value; LLK |
9.4 | PE | White, Carlson, et al., 1974 | Vertical value; LLK |
9.29 | PE | Robin, Taylor, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4+ | 11.7 ± 0.25 | ? | EI | Meisels, Park, et al., 1970 | RDSH |
C2H5+ | 12.25 | C2H3 | EI | Omura, 1961 | RDSH |
C3H3+ | 13.75 | ? | EI | Omura, 1961 | RDSH |
C3H5+ | 11.25 | CH3 | PI | Traeger, 1984 | LBLHLM |
C3H5+ | 11.33 | CH3 | EI | Lossing, 1971 | LLK |
C4H7+ | 11.19 | H | PI | Traeger, 1986 | LBLHLM |
C4H7+ | 11.32 | H | EI | Lossing, 1972 | LLK |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, 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
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
NIST MS number | 18914 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Scott, Ferguson, et al., 1944
Scott, R.B.; Ferguson, W.J.; Brickwedde, F.G.,
Thermodynamic properties of cis-2-butene from 15° to 1,500 K,
J. Res. NBS, 1944, 33, 1-20. [all data]
Todd and Parks, 1936
Todd, S.S.; Parks, G.S.,
Thermal data on organic compounds. XV. Some heat capacity, entropy and free energy data for the isomeric butenes,
J. Am. Chem. Soc., 1936, 58, 134-137. [all data]
Schlinger and Sage, 1952
Schlinger, W.G.; Sage, B.H.,
Isobaric heat capacities at bubble point. cis-2-butene, isopropylbenzene, and n-decane,
Ind. Eng. Chem., 1952, 44, 2454-2456. [all data]
Kistiakowsky, Ruhoff, et al., 1935
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of Organic Reactions II. Hydrogenation of Some Simpler Olefinic Hydrocarbons,
J. Am. Chem. Soc., 1935, 57, 876-82. [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 and Parks, 1936, 2
Todd, S.S.; Parks, G.S.,
Thermal Data on Organic Compounds XV. Some Heat Capacity, Entropy and Free Energy Data for the Isomeric Butenes,
J. Am. Chem. Soc., 1936, 58, 134. [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]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Ambrose, Cox, et al., 1960
Ambrose, D.; Cox, J.D.; Townsend, R.,
The critical temperatures of forty organic compounds,
Trans. Faraday Soc., 1960, 56, 1452. [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, Ferguson, et al., 1944, 2
Scott, R.B.; Ferguson, W.J.; Brickwedde, F.G.,
Thermodynamic properties of cis-2-butene from 15 degrees to 1,500 degrees K,
J. RES. NATL. BUR. STAN., 1944, 33, 1, 1-17, https://doi.org/10.6028/jres.033.001
. [all data]
Kistiakowsky, Ruhoff, et al., 1935, 2
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of organic reactions. II. Hydrogenation of some simpler olefinic hydrocarbons,
J. Am. Chem. Soc., 1935, 57, 876-882. [all data]
Hopkins, 1921
Hopkins, O.P.,
THE CHEMICAL INDUSTRY AND TRADE OF ENGLAND.,
J. Ind. Eng. Chem., 1921, 13, 3, 189-197, https://doi.org/10.1021/ie50135a007
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [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]
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]
Traeger, 1984
Traeger, J.C.,
A study of the allyl cation thermochemistry by photoionization mass spectrometry,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259. [all data]
Wood and Taylor, 1979
Wood, K.V.; Taylor, J.W.,
A photoionization mass spectrometric study of autoionization in ethylene and trans-2-butene,
Int. J. Mass Spectrom. Ion Phys., 1979, 30, 307. [all data]
Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J.,
eIonization energies of organic compounds by equilibrium measurements,
J. Am. Chem. Soc., 1978, 100, 6027. [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]
Lossing, 1972
Lossing, F.P.,
Free radicals by mass spectrometry. XLV. Ionization potentials and heats of formation of C3H3, C3H5, and C4H7 radicals and ions,
Can. J. Chem., 1972, 50, 3973. [all data]
Frost and Sandhu, 1971
Frost, D.C.; Sandhu, J.S.,
Ionization potentials of ethylene and some methyl-substituted ethylenes as determined by photoelectron spectroscopy,
Indian J. Chem., 1971, 9, 1105. [all data]
McDiarmid, 1969
McDiarmid, R.,
Rydberg progressions in cis- and trans-butene,
J. Chem. Phys., 1969, 50, 2328. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C.,
The effect of fluorine on the electronic spectra and ionization potentials of molecules,
Proc. Roy. Soc. (London), 1960, A258, 459. [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]
Wiberg, Ellison, et al., 1976
Wiberg, K.B.; Ellison, G.B.; Wendoloski, J.J.; Brundle, C.R.; Kuebler, N.A.,
Electronic states of organic molecules. 3. Photoelectron spectra of cycloalkenes and methylenecycloalkanes,
J. Am. Chem. Soc., 1976, 98, 7179. [all data]
Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K.,
Alkyl-induced, natural hypsochromic shifts of the 2A←2X and 2B←2X transitions of azulene and naphthalene radical cations,
Nouv. J. Chim., 1976, 1, 105. [all data]
Kimura, Katsumata, et al., 1975
Kimura, K.; Katsumata, S.; Yamazaki, T.; Wakabayashi, H.,
UV photoelectron spectra and sum rule consideration; out-of-plane orbitals of unsaturated compounds with planar-skeleton structure,
J. Electron Spectrosc. Relat. Phenom., 1975, 6, 41. [all data]
White, Carlson, et al., 1974
White, R.M.; Carlson, T.A.; Spears, D.P.,
Angular distribution of the photoelectron spectra for ethylene, propylene, butene and butadiene,
J. Electron Spectrosc. Relat. Phenom., 1974, 3, 59. [all data]
Robin, Taylor, et al., 1973
Robin, M.B.; Taylor, G.N.; Kuebler, N.A.; Bach, R.D.,
Planarity of the carbon skeleton in various alkylated olefins,
J. Org. Chem., 1973, 38, 1049. [all data]
Meisels, Park, et al., 1970
Meisels, G.G.; Park, J.Y.; Giessner, B.G.,
Ionization and dissociation of C4H8 isomers,
J. Am. Chem. Soc., 1970, 92, 254. [all data]
Omura, 1961
Omura, I.,
Mass spectra at low ionizing voltage and bond dissociation energies of molecular ions from hydrocarbons,
Bull. Chem. Soc. Japan, 1961, 34, 1227. [all data]
Lossing, 1971
Lossing, F.P.,
Free radicals by mass spectrometry. XLIII. Ionization potentials and ionic heats of formation for vinyl, allyl, and benzyl radicals,
Can. J. Chem., 1971, 49, 357. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy 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 Vc Critical volume ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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