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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Reaction thermochemistry data

Go To: Top, References, Notes

Data compiled as indicated in comments:
B - John E. Bartmess
MS - José A. Martinho Simões
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

C₄H₉^- + = Butane

By formula: C₄H₉^- + H⁺ = C₄H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1739. ± 8.4	kJ/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°	1745. ± 20.	kJ/mol	Bran	Peerboom, Rademaker, et al., 1992	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1703. ± 8.8	kJ/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°	1709. ± 21.	kJ/mol	H-TS	Peerboom, Rademaker, et al., 1992	gas phase; B

C₄H₉Li (l) + (g) = Butane (l) + (cr)

By formula: C₄H₉Li (l) + HBr (g) = C₄H₁₀ (l) + BrLi (cr)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-374.0 ± 2.0	kJ/mol	RSC	Holm, 1974	Please also see Pedley and Rylance, 1977. The reaction enthalpy was quoted from Pedley and Rylance, 1977. See Liebman, Martinho Simões, et al., 1995 for comments; MS

(g) + C₄H₉Li (l) = Butane (l) + (cr)

By formula: HBr (g) + C₄H₉Li (l) = C₄H₁₀ (l) + BrLi (cr)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-352.7 ± 2.0	kJ/mol	RSC	Holm, 1974	Please also see Pedley and Rylance, 1977. The reaction enthalpy was quoted from Pedley and Rylance, 1977. See Liebman, Martinho Simões, et al., 1995 for comments; MS

2 + = Butane

By formula: 2H₂ + C₄H₆ = C₄H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-272.4 ± 1.3	kJ/mol	Chyd	Conn, Kistiakowsky, et al., 1939	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -274.4 ± 0.54 kJ/mol; At 355 K; ALS

+ = Butane

By formula: H₂ + C₄H₈ = C₄H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-114.6 ± 0.42	kJ/mol	Chyd	Kistiakowsky, Ruhoff, et al., 1935	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -115.57 ± 0.088 kJ/mol; At 355 °K; ALS

+ = Butane

By formula: H₂ + C₄H₈ = C₄H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-118.5 ± 0.42	kJ/mol	Chyd	Kistiakowsky, Ruhoff, et al., 1935	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -119.54 ± 0.079 kJ/mol; At 355 °K; ALS

+ 2 = Butane

By formula: C₄H₆ + 2H₂ = C₄H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-236.7 ± 0.42	kJ/mol	Chyd	Kistiakowsky, Ruhoff, et al., 1936	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -238.8 ± 0.4 kJ/mol; At 355 °K; ALS

C₄H₉Li (l) + (g) = Butane (g) + HLiO (cr)

By formula: C₄H₉Li (l) + H₂O (g) = C₄H₁₀ (g) + HLiO (cr)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-240.2 ± 2.9	kJ/mol	RSC	Fowell and Mortimer, 1961	Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970, 2.; MS

C₄H₉ClMg (cr) + ( • 556) (solution) = Butane (g) + (Cl₂Mg • 900) (solution)

By formula: C₄H₉ClMg (cr) + (HCl • 556H₂O) (solution) = C₄H₁₀ (g) + (Cl₂Mg • 900H₂O) (solution)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-305.8 ± 1.8	kJ/mol	RSC	Genchel, Evstigneeva, et al., 1976	MS

C₄H₉BrMg (solution) + (g) = Butane (solution) + Br₂Mg (solution)

By formula: C₄H₉BrMg (solution) + HBr (g) = C₄H₁₀ (solution) + Br₂Mg (solution)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-292.5 ± 2.2	kJ/mol	RSC	Holm, 1981	solvent: Diethyl ether; MS

C₄H₉BrMg (solution) + (g) = Butane (solution) + Br₂Mg (solution)

By formula: C₄H₉BrMg (solution) + HBr (g) = C₄H₁₀ (solution) + Br₂Mg (solution)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-305.9 ± 2.2	kJ/mol	RSC	Holm, 1981	solvent: Diethyl ether; MS

C₅O₅W (g) + Butane (g) = C₉H₁₀O₅W (g)

By formula: C₅O₅W (g) + C₄H₁₀ (g) = C₉H₁₀O₅W (g)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-38. ± 13.	kJ/mol	EqG	Brown, Ishikawa, et al., 1990	Temperature range: ca. 300-350 K; MS

+ = Butane

By formula: C₄H₈ + H₂ = C₄H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-125.9 ± 0.42	kJ/mol	Chyd	Kistiakowsky, Ruhoff, et al., 1935	gas phase; At 355 °K; ALS

Butane =

By formula: C₄H₁₀ = C₄H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-9.699	kJ/mol	Eqk	Pines, Kvetinskas, et al., 1945	gas phase; Heat of isomerization; ALS

3 + = Butane

By formula: 3H₂ + C₄H₄ = C₄H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-422. ± 2.	kJ/mol	Chyd	Roth, Adamczak, et al., 1991	liquid phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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]

Holm, 1974
Holm, T., J. Organometal. Chem., 1974, 77, 27. [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brigton, 1977. [all data]

Liebman, Martinho Simões, et al., 1995
Liebman, J.F.; Martinho Simões, J.A.; Slayden, S.W., In Lithium Chemistry: A Theoretical and Experimental Overview Wiley: New York, Sapse, A.-M.; Schleyer, P. von Ragué, ed(s)., 1995. [all data]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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, 876-882. [all data]

Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene, J. Am. Chem. Soc., 1936, 58, 146-153. [all data]

Fowell and Mortimer, 1961
Fowell, P.A.; Mortimer, C.T., J. Chem. Soc., 1961, 3793.. [all data]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds in Academic Press, New York, 1970. [all data]

Genchel, Evstigneeva, et al., 1976
Genchel, V.G.; Evstigneeva, E.V.; Petrova, N.V., Zh. Fiz. Khim., 1976, 50, 1909. [all data]

Holm, 1981
Holm, T., J. Chem. Soc., Perkin Trans. II, 1981, 464.. [all data]

Brown, Ishikawa, et al., 1990
Brown, C.E.; Ishikawa, Y.; Hackett, P.A.; Rayner, D.M., J. Am. Chem. Soc., 1990, 112, 2530. [all data]

Pines, Kvetinskas, et al., 1945
Pines, H.; Kvetinskas, B.; Kassel, L.S.; Ipatieff, V.N., Determination of equilibrium constants for butanes and pentanes, J. Am. Chem. Soc., 1945, 67, 631-637. [all data]

Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R., Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld, Chem. Ber., 1991, 124, 2499-2521. [all data]

Notes

Go To: Top, Reaction thermochemistry data, References

Symbols used in this document:

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