1-Butene
- Formula: C4H8
- Molecular weight: 56.1063
- IUPAC Standard InChI: InChI=1S/C4H8/c1-3-4-2/h3H,1,4H2,2H3
- IUPAC Standard InChIKey: VXNZUUAINFGPBY-UHFFFAOYSA-N
- CAS Registry Number: 106-98-9
- 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: α-Butene; α-Butylene; But-1-ene; Butene-1; Ethylethylene; 1-Butylene; 1-C4H8
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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess
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Individual Reactions
=
By formula: C4H8 = C4H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -12.6 ± 0.84 | kJ/mol | Eqk | Meyer and Stroz, 1972 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -11.0 kJ/mol; At 300 K; ALS |
| ΔrH° | -12.4 ± 1.7 | kJ/mol | Eqk | Happel, Hnatow, et al., 1971 | gas phase; ALS |
| ΔrH° | -12.7 | kJ/mol | Eqk | Maccoll and Ross, 1965 | gas phase; GC; ALS |
| ΔrH° | -11.7 ± 0.84 | kJ/mol | Eqk | Golden, Egger, et al., 1964 | gas phase; ALS |
| ΔrH° | -11.5 | kJ/mol | Ciso | Levanova and Andreevskii, 1964 | gas phase; At 420.3 K; ALS |
C4H7- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1724. ± 8.4 | kJ/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
| ΔrH° | 1729. ± 20. | kJ/mol | Bran | Peerboom, Rademaker, et al., 1992 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1690. ± 8.8 | kJ/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; B |
| ΔrG° | 1695. ± 21. | kJ/mol | H-TS | Peerboom, Rademaker, et al., 1992 | gas phase; B |
+
=
By formula: C4H8 + Br2 = C4H8Br2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -120.9 | kJ/mol | Cm | Lister, 1941 | gas phase; Heat of bromination at 300 K; ALS |
| ΔrH° | -123.2 ± 0.84 | kJ/mol | Cm | Conn, Kistiakowsky, et al., 1938 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -123.8 ± 0.84 kJ/mol; At 355 °K; ALS |
+
=
By formula: HBr + C4H8 = C4H9Br
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -83.85 ± 0.50 | kJ/mol | Cm | Lacher, Billings, et al., 1952 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -84.3 ± 7.5 kJ/mol; Heat of hydrobromination at 367 K; ALS |
C4H7- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1707. ± 15. | kJ/mol | CIDT | Graul and Squires, 1990 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1674. ± 15. | kJ/mol | H-TS | Graul and Squires, 1990 | gas phase; B |
=
By formula: C4H8 = C4H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -10.6 ± 2.1 | kJ/mol | Eqk | Happel, Hnatow, et al., 1971 | gas phase; ALS |
| ΔrH° | -8.16 | kJ/mol | Ciso | Levanova and Andreevskii, 1964 | gas phase; At 420.3 K; ALS |
=
+
By formula: C4H8I2 = C4H8 + I2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 50.2 ± 6.3 | kJ/mol | Cm | Cline and Kistiakowsky, 1937 | gas phase; Heat of formation derived by Cox and Pilcher, 1970; ALS |
+
=
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -125.9 ± 0.42 | kJ/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1935 | gas phase; At 355 °K; ALS |
=
+
By formula: C4H9Cl = C4H8 + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 75.31 | kJ/mol | Eqk | Levanova and Andreevskii, 1964 | gas phase; At 420 K; ALS |
+
=
By formula: C4H8 + I2 = C4H8I2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -50.2 ± 6.3 | kJ/mol | Cm | Cline and Kistiakowsky, 1937 | gas phase; ALS |
=
+
By formula: C10H14O = C4H8 + C6H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 77.8 | kJ/mol | Cm | Kukui, Potolovskii, et al., 1973 | liquid phase; ALS |
=
+
By formula: C10H14O = C4H8 + C6H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 82.8 | kJ/mol | Cm | Kukui, Potolovskii, et al., 1973 | 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.
Meyer and Stroz, 1972
Meyer, E.F.; Stroz, D.G.,
Thermodynamics of n-butene isomerization,
J. Am. Chem. Soc., 1972, 94, 6344-6347. [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]
Happel, Hnatow, et al., 1971
Happel, J.; Hnatow, M.A.; Mezaki, R.,
Isomerization equilibrium constants of n-butenes,
J. Chem. Eng. Data, 1971, 16, 206-209. [all data]
Maccoll and Ross, 1965
Maccoll, A.; Ross, R.A.,
The hydrogen bromide catalyzed isomerization of n-butenes. I. equilibrium values,
J. Am. Chem. Soc., 1965, 87, 1169-1170. [all data]
Golden, Egger, et al., 1964
Golden, D.M.; Egger, K.W.; Benson, S.W.,
Iodine-catalyzed isomerization of olefins. I. Thermodynamics data from equilibrium studies of positional and geometrical isomerization of 1-butene and 2-butene,
J. Am. Chem. Soc., 1964, 86, 5416-5420. [all data]
Levanova and Andreevskii, 1964
Levanova, S.V.; Andreevskii, D.N.,
The equilibrium of 2-chlorobutane dehydrochlorination,
Neftekhimiya, 1964, 4, 329-336. [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]
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]
Lister, 1941
Lister, M.W.,
Heats of organic reactions. X. Heats of bromination of cyclic olefins,
J. Am. Chem. Soc., 1941, 63, 143-149. [all data]
Conn, Kistiakowsky, et al., 1938
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A.,
Heats of organic reactions. VII. Addition of halogens to olefins,
J. Am. Chem. Soc., 1938, 60, 2764-2771. [all data]
Lacher, Billings, et al., 1952
Lacher, J.R.; Billings, T.J.; Campion, D.E.,
Vapor phase heats of hydrobromination of the isomeric butenes,
J. Am. Chem. Soc., 1952, 74, 5291-52. [all data]
Graul and Squires, 1990
Graul, S.T.; Squires, R.R.,
Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions,
J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007
. [all data]
Cline and Kistiakowsky, 1937
Cline, J.E.; Kistiakowsky, G.B.,
The gaseous equilibrium of 1,2-diiodobutane, butene-1 and iodine,
J. Chem. Phys., 1937, 5, 990. [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]
Kukui, Potolovskii, et al., 1973
Kukui, N.M.; Potolovskii, L.A.; Vasileva, V.N.,
Thermochemical and thermodynamic calculation of the alkylation of phenol by normal α-olefins,
Khim. Tekhnol. Topl. Masel, 1973, 18, 10-13. [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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