2-Butene, (E)-
- Formula: C4H8
- Molecular weight: 56.1063
- IUPAC Standard InChIKey: IAQRGUVFOMOMEM-ONEGZZNKSA-N
- CAS Registry Number: 624-64-6
- 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. - Isotopologues:
- Stereoisomers:
- Other names: (E)-2-Butene; trans-Butene; trans-1,2-Dimethylethylene; trans-2-Butene; 2-trans-Butene; (E)-2-C4H8; 2-Butene, trans-; Butene-2,trans; t-Butene-2; (E)-but-2-ene
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Gas phase thermochemistry data
Go To: Top, 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 | -10.8 ± 1.0 | kJ/mol | Cm | Prosen, Maron, et al., 1951 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -2706.6 ± 0.96 | kJ/mol | Cm | Prosen, Maron, et al., 1951 | Corresponding ΔfHºgas = -10.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
36.12 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. Recommended entropies and heat capacities are in good agreement with those obtained from other statistical thermodynamics calculations [ Aston J.D., 1946, Kilpatrick J.E., 1946].; GT |
49.26 | 100. | ||
60.38 | 150. | ||
69.41 | 200. | ||
82.76 | 273.15 | ||
87.67 | 298.15 | ||
88.04 | 300. | ||
108.53 | 400. | ||
128.08 | 500. | ||
145.43 | 600. | ||
160.56 | 700. | ||
173.75 | 800. | ||
185.24 | 900. | ||
195.24 | 1000. | ||
203.93 | 1100. | ||
211.47 | 1200. | ||
218.02 | 1300. | ||
223.71 | 1400. | ||
228.67 | 1500. | ||
238.51 | 1750. | ||
245.64 | 2000. | ||
250.91 | 2250. | ||
254.88 | 2500. | ||
257.92 | 2750. | ||
260.28 | 3000. |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
87.78 | 298.60 | Kistiakowsky G.B., 1940 | GT |
94.93 | 332.90 | ||
102.63 | 371.50 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
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) | 9.10 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 747. | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 719.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.09 | PI | Traeger, 1986 | LBLHLM |
9.10 ± 0.02 | PI | Wood and Taylor, 1979 | LLK |
9.100 ± 0.008 | EQ | Lias and Ausloos, 1978 | LLK |
9.12 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.11 | PE | Clary, Lewis, et al., 1974 | LLK |
9.122 ± 0.005 | PE | Masclet, Grosjean, et al., 1973 | LLK |
9.09 | PE | Frost and Sandhu, 1971 | LLK |
9.137 | S | McDiarmid, 1969 | RDSH |
9.11 | PE | Haselbach, Hashmall, et al., 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 |
9.37 | PE | Kimura, Katsumata, et al., 1975 | Vertical value; LLK |
9.5 | PE | White, Carlson, et al., 1974 | Vertical value; LLK |
9.32 | PE | Robin, Taylor, et al., 1973 | Vertical value; LLK |
9.11 | PE | Brundle, Robin, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4+ | 11.8 ± 0.25 | ? | EI | Meisels, Park, et al., 1970 | RDSH |
C3H5+ | 11.30 | CH3 | PI | Traeger, 1984 | LBLHLM |
C4H7+ | 11.24 | H | PI | Traeger, 1986 | LBLHLM |
Ion clustering data
Go To: Top, Gas phase 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: C3H9Si+ + C4H8 = (C3H9Si+ • C4H8)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 129. | kJ/mol | PHPMS | Li and Stone, 1989 | gas phase; condensation |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 174. | J/mol*K | PHPMS | Li and Stone, 1989 | gas phase; condensation |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase 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.
Prosen, Maron, et al., 1951
Prosen, E.J.; Maron, F.W.; Rossini, F.D.,
Heats of combustion, formation, and insomerization of ten C4 hydrocarbons,
J. Res. NBS, 1951, 46, 106-112. [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]
Aston J.D., 1946
Aston J.D.,
Thermodynamic properties of gaseous 1,3-butadiene and normal butenes above 25 C. Equilibria in the system 1,3-butadiene, n-butenes, and n-butane,
J. Chem. Phys., 1946, 14, 67-79. [all data]
Kilpatrick J.E., 1946
Kilpatrick J.E.,
Heat content, free energy function, entropy, and heat capacity of ethylene, propylene, and the four butenes to 1500 K,
J. Res. Nat. Bur. Stand, 1946, 37, 163-171. [all data]
Kistiakowsky G.B., 1940
Kistiakowsky G.B.,
Gaseous heat capacities. III,
J. Chem. Phys., 1940, 8, 618-622. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [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]
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]
Clary, Lewis, et al., 1974
Clary, D.C.; Lewis, A.A.; Morland, D.; Murrell, J.N.; Heilbronner, E.,
Ionization potentials of cycloalkenes,
J. Chem. Soc. Faraday Trans. 2, 1974, 70, 1889. [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]
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]
Haselbach, Hashmall, et al., 1969
Haselbach, E.; Hashmall, J.A.; Heilbronner, E.; Hornung, V.,
The interaction between the lone pairs in azomethane,
Angew. Chem. Intern. Ed., 1969, 8, 878. [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]
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]
Brundle, Robin, et al., 1972
Brundle, C.R.; Robin, M.B.; Kuebler, N.A.; Basch, H.,
Perfluoro effect in photoelectron spectroscopy. I. Nonaromatic molecules,
J. Am. Chem. Soc., 1972, 94, 1451. [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]
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]
Li and Stone, 1989
Li, X.; Stone, J.A.,
Determination of the beta silicon effect from a mass spectrometric study of the association of trimethylsilylium ion with alkenes,
J. Am. Chem. Soc., 1989, 111, 15, 5586, https://doi.org/10.1021/ja00197a013
. [all data]
Notes
Go To: Top, Gas phase 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 IE (evaluated) Recommended ionization energy ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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