Butane
- Formula: C4H10
- Molecular weight: 58.1222
- 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 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:
B - John E. Bartmess
MS - José A. Martinho Simões
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C4H9- + =
By formula: C4H9- + H+ = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 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 |
ΔrH° | 417.1 ± 4.8 | kcal/mol | Bran | Peerboom, Rademaker, et al., 1992 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 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 |
ΔrG° | 408.5 ± 4.9 | kcal/mol | H-TS | Peerboom, Rademaker, et al., 1992 | gas phase; B |
C4H9Li (l) + (g) = (l) + (cr)
By formula: C4H9Li (l) + HBr (g) = C4H10 (l) + BrLi (cr)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -89.39 ± 0.48 | kcal/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) = (l) + (cr)
By formula: HBr (g) + C4H9Li (l) = C4H10 (l) + BrLi (cr)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -84.30 ± 0.48 | kcal/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 |
By formula: 2H2 + C4H6 = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -65.10 ± 0.30 | kcal/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -65.58 ± 0.13 kcal/mol; At 355 K; ALS |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -27.38 ± 0.10 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1935 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -27.621 ± 0.021 kcal/mol; At 355 °K; ALS |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28.33 ± 0.10 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1935 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -28.570 ± 0.019 kcal/mol; At 355 °K; ALS |
By formula: C4H6 + 2H2 = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -56.57 ± 0.10 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -57.1 ± 0.1 kcal/mol; At 355 °K; ALS |
C4H9Li (l) + (g) = (g) + HLiO (cr)
By formula: C4H9Li (l) + H2O (g) = C4H10 (g) + HLiO (cr)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -57.41 ± 0.69 | kcal/mol | RSC | Fowell and Mortimer, 1961 | Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970, 2.; MS |
C4H9ClMg (cr) + ( • 556) (solution) = (g) + (Cl2Mg • 900) (solution)
By formula: C4H9ClMg (cr) + (HCl • 556H2O) (solution) = C4H10 (g) + (Cl2Mg • 900H2O) (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -73.09 ± 0.43 | kcal/mol | RSC | Genchel, Evstigneeva, et al., 1976 | MS |
C4H9BrMg (solution) + (g) = (solution) + Br2Mg (solution)
By formula: C4H9BrMg (solution) + HBr (g) = C4H10 (solution) + Br2Mg (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -69.91 ± 0.53 | kcal/mol | RSC | Holm, 1981 | solvent: Diethyl ether; MS |
C4H9BrMg (solution) + (g) = (solution) + Br2Mg (solution)
By formula: C4H9BrMg (solution) + HBr (g) = C4H10 (solution) + Br2Mg (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -73.11 ± 0.53 | kcal/mol | RSC | Holm, 1981 | solvent: Diethyl ether; MS |
C5O5W (g) + (g) = C9H10O5W (g)
By formula: C5O5W (g) + C4H10 (g) = C9H10O5W (g)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -9.1 ± 3.0 | kcal/mol | EqG | Brown, Ishikawa, et al., 1990 | Temperature range: ca. 300-350 K; MS |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -30.10 ± 0.10 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1935 | gas phase; At 355 °K; ALS |
By formula: C4H10 = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -2.318 | kcal/mol | Eqk | Pines, Kvetinskas, et al., 1945 | gas phase; Heat of isomerization; ALS |
By formula: 3H2 + C4H4 = C4H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -100.8 ± 0.5 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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