1,3-Butadiene
- Formula: C4H6
- Molecular weight: 54.0904
- IUPAC Standard InChI: InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2
- IUPAC Standard InChIKey: KAKZBPTYRLMSJV-UHFFFAOYSA-N
- CAS Registry Number: 106-99-0
- 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,γ-Butadiene; Biethylene; Bivinyl; Buta-1,3-diene; Butadiene; Divinyl; Erythrene; Pyrrolylene; Vinylethylene; CH2=CHCH=CH2; Butadieen; Buta-1,3-dieen; Butadien; Buta-1,3-dien; NCI-C50602
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 26.00 ± 0.19 | kcal/mol | Cm | Prosen, Maron, et al., 1951 | ALS |
| ΔfH°gas | 26.75 ± 0.23 | kcal/mol | Ccb | Prosen and Rossini, 1945 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°gas | -607.16 ± 0.18 | kcal/mol | Cm | Prosen, Maron, et al., 1951 | Corresponding ΔfHºgas = 26.01 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 8.387 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. Recommended values are in excellent agreement with experiment and other statistically calculated values [ Sverdlov L.M., 1962, Compton D.A.C., 1976]. Discrepancies with earlier calculations [ Aston J.D., 1946] and [ Godnev I., 1947] amount to 4.7 and 2.7 J/mol*K, respectively, in S(T) and 3.6 and 2.4 J/mol*K in Cp(T).; GT |
| 9.873 | 100. | ||
| 11.54 | 150. | ||
| 13.66 | 200. | ||
| 17.61 | 273.15 | ||
| 19.08 | 298.15 | ||
| 19.18 | 300. | ||
| 24.723 | 400. | ||
| 29.180 | 500. | ||
| 32.627 | 600. | ||
| 35.382 | 700. | ||
| 37.684 | 800. | ||
| 39.656 | 900. | ||
| 41.372 | 1000. | ||
| 42.868 | 1100. | ||
| 44.178 | 1200. | ||
| 45.325 | 1300. | ||
| 46.331 | 1400. | ||
| 47.213 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | 21.63 ± 0.23 | kcal/mol | Ccb | Prosen and Rossini, 1945 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -602.79 ± 0.23 | kcal/mol | Ccb | Prosen and Rossini, 1945 | Corresponding ΔfHºliquid = 21.64 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 47.562 | cal/mol*K | N/A | Scott, Meyers, et al., 1945 | At vapor pressure of 2105 Torr.; DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 29.553 | 298.15 | Scott, Meyers, et al., 1945 | T = 15 to 303 K.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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
RCD - Robert C. Dunbar
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
+ 2
=
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 |
C4H5- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 399.5 ± 3.1 | kcal/mol | G+TS | Devisser, Dekoning, et al., 1995 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 391.3 ± 3.0 | kcal/mol | IMRB | Devisser, Dekoning, et al., 1995 | gas phase; B |
+
= (
•
)
By formula: Na+ + C4H6 = (Na+ • C4H6)
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 10.3 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
(CAS Reg. No. 88032-19-3 • 4294967295) +
= CAS Reg. No. 88032-19-3
By formula: (CAS Reg. No. 88032-19-3 • 4294967295C4H6) + C4H6 = CAS Reg. No. 88032-19-3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 14.7 ± 2.1 | kcal/mol | N/A | DePuy, Gronert, et al., 1989 | gas phase; B |
=
+
By formula: C8H8O3 = C4H6 + C4H2O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 67.79 ± 0.23 | kcal/mol | Cm | Ghitau, Ciopec, et al., 1983 | solid phase; At 65 to 90°C; ALS |
+
=
By formula: C4H6 + O2S = C4H6O2S
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -17.9 | kcal/mol | Eqk | Mackle and McNally, 1969 | gas phase; ALS |
+
=
By formula: C4H6 + C4H2O3 = C8H8O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -67.788 | kcal/mol | Cm | Ghitau, Ciopec, et al., 1983 | liquid phase; ALS |
+
=
By formula: C4H6 + O2S = C4H6O2S
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -16.5 | kcal/mol | Eqk | Mackle and McNally, 1969 | gas phase; ALS |
=
By formula: C4H6 = C4H6
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 12.78 ± 0.16 | kcal/mol | Ccb | Prosen, Maron, et al., 1949 | gas phase; ALS |
+
= (
•
)
By formula: Au+ + C4H6 = (Au+ • C4H6)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | >75. | kcal/mol | IMRB | Schroeder, Hrusak, et al., 1995 | RCD |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
Sverdlov L.M., 1962
Sverdlov L.M.,
Calculation of thermodynamic functions of gaseous 1,3-butadiene from spectroscopic data,
Zh. Fiz. Khim., 1962, 36, 2765-2767. [all data]
Compton D.A.C., 1976
Compton D.A.C.,
Conformations of conjugated hydrocarbons. Part 1. A spectroscopic and thermodynamic study of buta-1,3-diene and 2-methylbuta-1,3-diene,
J. Chem. Soc. Perkin Trans. 2, 1976, 1666-1671. [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]
Godnev I., 1947
Godnev I.,
Thermodynamic functions of divinyl and equilibrium constant of formation of divinyl from alcohol,
Zh. Fiz. Khim., 1947, 21, 799-809. [all data]
Scott, Meyers, et al., 1945
Scott, R.B.; Meyers, C.H.; Rands, R.D., Jr.; Brickwedde, F.G.; Bekkedahl, N.,
Thermodynamic properties of 1,3-butadiene in the solid, liquid, and vapor states,
J. Res. NBS, 1945, 35, 39-85. [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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Devisser, Dekoning, et al., 1995
Devisser, S.P.; Dekoning, L.J.; Vanderhart, W.J.; Nibbering, N.M.M.,
Chemical properties of butadienyl anions in the gas-phase,
Recl. Trav. Chim. Pays-Bas, 1995, 114, 6, 267, https://doi.org/10.1002/recl.19951140603
. [all data]
McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G.,
An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions,
Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7
. [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]
Ghitau, Ciopec, et al., 1983
Ghitau, M.; Ciopec, M.; Pintea, O.,
Study on Diels-Alder reaction for the synthesis of tetrahydrophthalic anhydride,
Rev. Chim. (Bucharest), 1983, 34, 299-305. [all data]
Mackle and McNally, 1969
Mackle, H.; McNally, D.V.,
Studies in the thermochemistry of sulphones. Part 9 - Thermochemistry of the butadiene and isoprene sulphones,
Trans. Faraday Soc., 1969, 65, 1738-1741. [all data]
Prosen, Maron, et al., 1949
Prosen, E.J.; Maron, F.W.; Rossini, F.D.,
Heat of isomerization of the two butadienes,
J. Res. NBS, 1949, 42, 269-275. [all data]
Schroeder, Hrusak, et al., 1995
Schroeder, D.; Hrusak, J.; Hertwig, R.H.; Koch, W.; Schwerdtfeger, P.; Schwarz, H.,
Experimental and Theoretical Studies of Gold(I) Complexes Au(L)+ (L=H2O, CO, NH3, C2H4, C3H6, C4H6, C6H6, C6F6),
Organometallics, 1995, 14, 1, 312, https://doi.org/10.1021/om00001a045
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions T Temperature ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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