2-Butene, (Z)-

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-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
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Stereoisomers:
- 2-Butene
- 2-Butene, (E)-
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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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References, Notes

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	-7.7 ± 1.3	kJ/mol	Cm	Prosen, Maron, et al., 1951	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-2709.8 ± 1.2	kJ/mol	Cm	Prosen, Maron, et al., 1951	Corresponding Δ_fHº_gas = -7.57 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
45.01	50.	Thermodynamics Research Center, 1997	p=1 bar. The difference between recommended values and obtained by [ Aston J.D., 1946] is inside the range of uncertainties of these two statistical calculations. The values of S and Cp calculated by [ Scott R.B., 1944] and [ Kilpatrick J.E., 1946] are little lower than recommended ones.; GT
51.23	100.
55.45	150.
61.73	200.
74.89	273.15
80.15	298.15
80.55	300.
102.73	400.
123.64	500.
141.91	600.
157.66	700.
171.27	800.
183.06	900.
193.30	1000.
202.18	1100.
209.90	1200.
216.59	1300.
222.41	1400.
227.48	1500.
237.55	1750.
244.85	2000.
250.26	2250.
254.33	2500.
257.45	2750.
259.87	3000.

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
70.8 ± 1.6	250.	Scott R.B., 1944	Please also see Kistiakowsky G.B., 1940.; GT
71.1 ± 1.6	255.
71.7 ± 1.7	260.
72.3 ± 1.7	265.
72.9 ± 1.7	270.
73.9 ± 1.7	275.
74.7 ± 1.7	280.
75.9 ± 1.8	285.
77.2 ± 1.8	290.
78.5 ± 1.8	295.
81.13 ± 0.16	298.58
79.9 ± 1.8	300.
88.24 ± 0.18	332.85
96.27 ± 0.19	371.24

Condensed phase thermochemistry data

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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

C_p,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.

Gas phase ion energetics data

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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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, 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]

Scott R.B., 1944
Scott R.B., Thermodynamic properties of cis-2-butene from 15 to 1500 K, J. Res. Nat. Bur. Stand., 1944, 33, 1-20. [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]

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]

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

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Symbols used in this document:

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

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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