Butane

Formula: C₄H₁₀
Molecular weight: 58.1222
IUPAC Standard InChI: InChI=1S/C4H10/c1-3-4-2/h3-4H2,1-2H3
IUPAC Standard InChIKey: IJDNQMDRQITEOD-UHFFFAOYSA-N
CAS Registry Number: 106-97-8
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.
Other names: n-Butane; Diethyl; Freon 600; Liquefied petroleum gas; LPG; n-C4H10; Butanen; Butani; Methylethylmethane; UN 1011; A 21; HC 600; HC 600 (hydrocarbon); R 600; R 600 (alkane)
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Gas phase thermochemistry data

Go To: Top, 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	-30.03 ± 0.16	kcal/mol	Ccb	Pittam and Pilcher, 1972	ALS
Δ_fH°_gas	-30.37 ± 0.16	kcal/mol	Cm	Prosen, Maron, et al., 1951	see Prosen and Rossini, 1945; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-687.75 ± 0.15	kcal/mol	Ccb	Pittam and Pilcher, 1972	Corresponding Δ_fHº_gas = -30.03 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_gas	-687.42 ± 0.15	kcal/mol	Cm	Prosen, Maron, et al., 1951	see Prosen and Rossini, 1945; Corresponding Δ_fHº_gas = -30.36 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_gas	-687.94 ± 0.15	kcal/mol	Ccb	Rossini, 1934	Corresponding Δ_fHº_gas = -29.84 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
9.099	50.	Chen S.S., 1975	Recommended values are in good agreement with those calculated by [ Pitzer K.S., 1944, Pitzer K.S., 1946].; GT
13.23	100.
16.09	150.
18.27	200.
22.06	273.15
23.54	298.15
23.65	300.
29.821	400.
35.531	500.
40.459	600.
44.699	700.
48.370	800.
51.561	900.
54.340	1000.
56.759	1100.
58.860	1200.
60.691	1300.
62.280	1400.
63.671	1500.

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
26.429	344.9	Dailey B.P., 1943	Other experimental values of heat capacity [ Sage B.H., 1937] are believed to be less reliable, see [ Chen S.S., 1975].; GT
27.469	359.6
29.099	387.5
32.980	451.6
36.809	521.0
38.781	561.3
40.710	600.8
44.419	692.6

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, References, Notes

Data evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	10.53 ± 0.02	eV	N/A	N/A	L

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.57	EST	Luo and Pacey, 1992	LL
10.53 ± 0.10	EVAL	Lias, 1982	LBLHLM
10.35 ± 0.15	EQ	Mautner(Meot-Ner), Sieck, et al., 1981	LLK
10.6 ± 0.1	PE	Bieri, Burger, et al., 1977	LLK
10.61	EQ	Lias, Ausloos, et al., 1976	LLK
10.87 ± 0.05	EI	Flesch and Svec, 1973	LLK
10.89	EI	Matsumoto, Taniguchi, et al., 1970	RDSH
10.67	PI	Dewar and Worley, 1969	RDSH
10.55 ± 0.05	PI	Chupka and Berkowitz, 1967	RDSH
10.50	PI	Al-Joboury and Turner, 1964	RDSH
10.55 ± 0.05	PI	Steiner, Giese, et al., 1961	RDSH
10.63 ± 0.03	PI	Watanabe, 1957	RDSH
11.09	PE	Kimura, Katsumata, et al., 1981	Vertical value; LLK
11.2	PE	Bieri and Asbrink, 1980	Vertical value; LLK
11.2 ± 0.1	PE	Bieri, Burger, et al., 1977	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CH₃⁺	29.7 ± 0.2	?	EI	Olmsted, Street, et al., 1964	RDSH
C₂H₄⁺	~11.65	C₂H₆	PI	Chupka and Berkowitz, 1967	RDSH
C₂H₅⁺	12.55	C₂H₅	EI	Omura, 1961	RDSH
C₃H₅⁺	13.40	?	EI	Omura, 1961	RDSH
C₃H₆⁺	11.15	CH₄	EI	Wolkoff and Holmes, 1978	LLK
C₃H₆⁺	11.06	CH₄	EI	Matsumoto, Taniguchi, et al., 1970	RDSH
C₃H₆⁺	11.18	CH₄	PI	Chupka and Berkowitz, 1967	RDSH
C₃H₆⁺	11.16 ± 0.03	CH₄	PI	Steiner, Giese, et al., 1961	RDSH
C₃H₇⁺	11.2	CH₃	EI	Wolkoff and Holmes, 1978	LLK
C₃H₇⁺	11.09	CH₃	EI	Matsumoto, Taniguchi, et al., 1970	RDSH
C₃H₇⁺	11.10 ± 0.05	CH₃	EI	Williams and Hamill, 1968	RDSH
C₃H₇⁺	11.18	CH₃	PI	Chupka and Berkowitz, 1967	RDSH
C₃H₇⁺	11.19 ± 0.02	CH₃	PI	Steiner, Giese, et al., 1961	RDSH
C₄H₉⁺	10.9 ± 0.1	H^-	PI	Chupka and Berkowitz, 1967	RDSH
C₄H₉⁺	11.7 ± 0.1	H	PI	Chupka and Berkowitz, 1967	RDSH
H₃⁺	31. ± 1.	?	EI	Fuchs, 1972	LLK

De-protonation reactions

C₄H₉^- + = Butane

By formula: C₄H₉^- + H⁺ = C₄H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	415.7 ± 2.0	kcal/mol	Bran	DePuy, Gronert, et al., 1989	gas phase; The HOF(Et(Me)N.) in Seetula, Russell, et al., 1990 gives BDE(N-H) = 99 kcal/mol, ca. 5 kcal/mol too strong; B
Δ_rH°	417.1 ± 4.8	kcal/mol	Bran	Peerboom, Rademaker, et al., 1992	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	407.1 ± 2.1	kcal/mol	H-TS	DePuy, Gronert, et al., 1989	gas phase; The HOF(Et(Me)N.) in Seetula, Russell, et al., 1990 gives BDE(N-H) = 99 kcal/mol, ca. 5 kcal/mol too strong; B
Δ_rG°	408.5 ± 4.9	kcal/mol	H-TS	Peerboom, Rademaker, et al., 1992	gas phase; B

References

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

Pittam and Pilcher, 1972
Pittam, D.A.; Pilcher, G., Measurements of heats of combustion by flame calorimetry. Part 8.-Methane, ethane, propane, n-butane and 2-methylpropane, J. Chem. Soc. Faraday Trans. 1, 1972, 68, 2224-2229. [all data]

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]

Prosen and Rossini, 1945
Prosen, E.J.; Rossini, F.D., Heats of formation and combustion of 1,3-butadiene and styrene, J. Res. NBS, 1945, 34, 59-63. [all data]

Rossini, 1934
Rossini, F.D., Calorimetric determination of the heats of combustion of ethane, propane, normal butane, and normal pentane, J. Res. NBS, 1934, 12, 735-750. [all data]

Chen S.S., 1975
Chen S.S., Ideal gas thermodynamic properties and isomerization of n-butane and isobutane, J. Phys. Chem. Ref. Data, 1975, 4, 859-869. [all data]

Pitzer K.S., 1944
Pitzer K.S., Thermodynamics of gaseous paraffins. Specific heat and related properties, Ind. Eng. Chem., 1944, 36, 829-831. [all data]

Pitzer K.S., 1946
Pitzer K.S., The entropies and related properties of branched paraffin hydrocarbons, Chem. Rev., 1946, 39, 435-447. [all data]

Dailey B.P., 1943
Dailey B.P., Heat capacities and hindered rotation in n-butane and isobutane, J. Am. Chem. Soc., 1943, 65, 44-46. [all data]

Sage B.H., 1937
Sage B.H., Phase equilibria in hydrocarbon systems. XX. Isobaric heat capacity of gaseous propane, n-butane, isobutane, and n-pentane, Ind. Eng. Chem., 1937, 29, 1309-1314. [all data]

Luo and Pacey, 1992
Luo, Y.-R.; Pacey, P.D., Effects of alkyl substitution on ionization energies of alkanes and haloalkanes and on heats of formation of their molecular cations. Part 2. Alkanes and chloro-, bromo- and iodoalkanes, Int. J. Mass Spectrom. Ion Processes, 1992, 112, 63. [all data]

Lias, 1982
Lias, S.G., Thermochemical information from ion-molecule rate constants, Ion Cyclotron Reson. Spectrom. 1982, 1982, 409. [all data]

Mautner(Meot-Ner), Sieck, et al., 1981
Mautner(Meot-Ner), M.; Sieck, L.W.; Ausloos, P., Ionization of normal alkanes: Enthalpy, entropy, structural, and isotope effects, J. Am. Chem. Soc., 1981, 103, 5342. [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]

Lias, Ausloos, et al., 1976
Lias, S.G.; Ausloos, P.; Horvath, Z., Charge transfer reactions in alkane and cycloalkane systems. Estimated ionization potentials, Int. J. Chem. Kinet., 1976, 8, 725. [all data]

Flesch and Svec, 1973
Flesch, G.D.; Svec, H.J., Fragmentation reactions in the mass spectrometer for C₂-C₅ alkanes, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 1187. [all data]

Matsumoto, Taniguchi, et al., 1970
Matsumoto, A.; Taniguchi, S.; Hayakawa, T., Studies of dissociation of hydrogen and n-butane metastable ions by a pulsed ion source in Recent Developments in Mass Spectrometry, ed. K. Ogata and T. Hayakawa, Univ. Park Press, Baltimore, MD, 1970, 820. [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]

Chupka and Berkowitz, 1967
Chupka, W.A.; Berkowitz, J., Photoionization of ethane, propane, and n-butane with mass analysis, J. Chem. Phys., 1967, 47, 2921. [all data]

Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W., Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials, J. Chem. Soc., 1964, 4434. [all data]

Steiner, Giese, et al., 1961
Steiner, B.; Giese, C.F.; Inghram, M.G., Photoionization of alkanes. Dissociation of excited molecular ions, J. Chem. Phys., 1961, 34, 189. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Bieri and Asbrink, 1980
Bieri, G.; Asbrink, L., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1980, 20, 149. [all data]

Olmsted, Street, et al., 1964
Olmsted, J., III; Street, K., Jr.; Newton, A.S., Excess-kinetic-energy ions in organic mass spectra, J. Chem. Phys., 1964, 40, 2114. [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]

Wolkoff and Holmes, 1978
Wolkoff, P.; Holmes, J.L., Fragmentations of alkane molecular ions, J. Am. Chem. Soc., 1978, 100, 7346. [all data]

Williams and Hamill, 1968
Williams, J.M.; Hamill, W.H., Ionization potentials of molecules and free radicals and appearance potentials by electron impact in the mass spectrometer, J. Chem. Phys., 1968, 49, 4467. [all data]

Fuchs, 1972
Fuchs, R., Die kinetische energie ionisierter molekulfragmente VII. H₃ ALS fragmention bei der elektronenstrossionisierung von kohlenwasserstoffen, Int. J. Mass Spectrom. Ion Processes, 1972, 8, 193. [all data]

DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]

Seetula, Russell, et al., 1990
Seetula, J.A.; Russell, J.J.; Gutman, D., Kinetics and Thermochemistry of the Reactions of Alkyl Radicals with HI: A Reconciliation of the Alkyl Radical Heats of Formation, J. Am. Chem. Soc., 1990, 112, 4, 1347, https://doi.org/10.1021/ja00160a009 . [all data]

Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [all data]

Notes

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

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_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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