1,3-Butadiene
- Formula: C4H6
- Molecular weight: 54.0904
- 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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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
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
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, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature 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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