2-Butene, (E)-

Formula: C₄H₈
Molecular weight: 56.1063
IUPAC Standard InChI: InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3/b4-3+
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:
- (E)-2-Butene-d8
Stereoisomers:
- 2-Butene
- 2-Butene, (Z)-
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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Other data available:
Data at other public NIST sites:
- Electron-Impact Ionization Cross Sections (on physics web site)
- Gas Phase Kinetics Database
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Gas phase thermochemistry data

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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
Δ_fH°_gas	-2.58 ± 0.24	kcal/mol	Cm	Prosen, Maron, et al., 1951	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-646.90 ± 0.23	kcal/mol	Cm	Prosen, Maron, et al., 1951	Corresponding Δ_fHº_gas = -2.56 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
8.633	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
11.77	100.
14.43	150.
16.59	200.
19.78	273.15
20.95	298.15
21.04	300.
25.939	400.
30.612	500.
34.759	600.
38.375	700.
41.527	800.
44.273	900.
46.663	1000.
48.740	1100.
50.543	1200.
52.108	1300.
53.468	1400.
54.653	1500.
57.005	1750.
58.709	2000.
59.969	2250.
60.918	2500.
61.644	2750.
62.208	3000.

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
20.98	298.60	Kistiakowsky G.B., 1940	GT
22.69	332.90
24.529	371.50

Gas phase ion energetics data

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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)	179.	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	172.1	kcal/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

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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

C₃H₉Si⁺ + 2-Butene, (E)- = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₄H₈ = (C₃H₉Si⁺ • C₄H₈)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	30.9	kcal/mol	PHPMS	Li and Stone, 1989	gas phase; condensation
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	41.5	cal/mol*K	PHPMS	Li and Stone, 1989	gas phase; condensation

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

GAS (150 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm^-1 resolution

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

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

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
IE (evaluated)	Recommended ionization energy
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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