1,3-Butadiene - The NIST WebBook

1,3-Butadiene

• Formula: C4H6
• Molecular weight: 54.0904
• IUPAC Standard InChI: InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2 Copy
• IUPAC Standard InChIKey: KAKZBPTYRLMSJV-UHFFFAOYSA-N Copy
• 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 View 3d structure (requires JavaScript / HTML 5)
• 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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• Information on this page:
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
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  • Ion clustering data
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Reaction thermochemistry data

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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°	-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

C4H5- + =

By formula: C4H5- + H+ = C4H6

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	1672. ± 13.	kJ/mol	G+TS	Devisser, Dekoning, et al., 1995	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
ΔrG°	1637. ± 13.	kJ/mol	IMRB	Devisser, Dekoning, et al., 1995	gas phase; B

+ = ( • )

By formula: Na+ + C4H6 = (Na+ • C4H6)

Free energy of reaction

ΔrG° (kJ/mol)	T (K)	Method	Reference	Comment
43.1	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°	61.5 ± 8.8	kJ/mol	N/A	DePuy, Gronert, et al., 1989	gas phase; B

= +

By formula: C8H8O3 = C4H6 + C4H2O3

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	283.62 ± 0.96	kJ/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°	-74.9	kJ/mol	Eqk	Mackle and McNally, 1969	gas phase; ALS

+ =

By formula: C4H6 + C4H2O3 = C8H8O3

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-283.62	kJ/mol	Cm	Ghitau, Ciopec, et al., 1983	liquid phase; ALS

+ =

By formula: C4H6 + O2S = C4H6O2S

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-69.0	kJ/mol	Eqk	Mackle and McNally, 1969	gas phase; ALS

=

By formula: C4H6 = C4H6

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	53.47 ± 0.67	kJ/mol	Ccb	Prosen, Maron, et al., 1949	gas phase; ALS

+ = ( • )

By formula: Au+ + C4H6 = (Au+ • C4H6)

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	>310.	kJ/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

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• 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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