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
  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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • Vibrational and/or electronic energy levels
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Electron-Impact Ionization Cross Sections (on physics web site)
  • Gas Phase Kinetics Database
• Options:
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Gas phase 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Condensed phase 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    T_r = reduced temperature (T / T_c)

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Entropy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

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

C₄H₅^- +  =

By formula: C₄H₅^- + H⁺ = C₄H₆

 +  = ( • )

By formula: Na⁺ + C₄H₆ = (Na⁺ • C₄H₆)

Free energy of reaction

(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

=  + 

By formula: C₈H₈O₃ = C₄H₆ + C₄H₂O₃

 +  =

By formula: C₄H₆ + O₂S = C₄H₆O₂S

 +  =

By formula: C₄H₆ + C₄H₂O₃ = C₈H₈O₃

 +  =

By formula: C₄H₆ + O₂S = C₄H₆O₂S

=

By formula: C₄H₆ = C₄H₆

 +  = ( • )

By formula: Au⁺ + C₄H₆ = (Au⁺ • C₄H₆)

Henry's Law 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 by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₄H₆⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₅^- +  =

By formula: C₄H₅^- + H⁺ = C₄H₆

Ion clustering 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 by: Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

By formula: Au⁺ + C₄H₆ = (Au⁺ • C₄H₆)

 +  = ( • )

By formula: Na⁺ + C₄H₆ = (Na⁺ • C₄H₆)

Free energy of reaction

Vibrational and/or electronic energy levels

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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 by: Takehiko Shimanouchi

Symmetry:   C_2h     Symmetry Number σ = 2

Source: Shimanouchi, 1972

Notes

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, Vibrational and/or electronic energy levels, 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]

Tsonopoulos and Ambrose, 1996
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons, J. Chem. Eng. Data, 1996, 41, 645-656. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Reid, 1972
Reid, Robert C., Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00, AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637 . [all data]

Prosen and Rossini, 1945, 2
Prosen, E.J.; Rossini, F.D., Heats of formation and combustion of 1,3-butadiene and styrene, J. RES. NATL. BUR. STAN., 1945, 34, 1, 59-17, https://doi.org/10.6028/jres.034.031 . [all data]

Stephenson and Malanowski, 1987
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Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Heisig, 1933
Heisig, G.B., Action of Radon on Some Unsaturated Hydrocarbons. III. Vinylacetylene and Butadiene, J. Am. Chem. Soc., 1933, 55, 6, 2304-2311, https://doi.org/10.1021/ja01333a015 . [all data]

Vaughan, 1932
Vaughan, William E., THE HOMOGENEOUS THERMAL POLYMERIZATION OF 1,3-BUTADIENE, J. Am. Chem. Soc., 1932, 54, 10, 3863-3876, https://doi.org/10.1021/ja01349a008 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Mallard, Miller, et al., 1983
Mallard, W.G.; Miller, J.H.; Smyth, K.C., The ns Rydberg series of 1,3-trans-butadiene observed using multiphoton ionization, J. Chem. Phys., 1983, 79, 5900. [all data]

Masclet, Mouvier, et al., 1981
Masclet, P.; Mouvier, G.; Bocquet, J.F., Effets electroniques et effets steriques dus a la substitution alcoyle dans les dienes conjugues, J. Chim. Phys., 1981, 78, 99. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

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Dannacher, J.; Flamme, J.P.; Stadelmann, J.P.; Vogt, J., Unimolecular fragmentations of internal energy selected 1,3-butadiene cations, Chem. Phys., 1980, 51, 189. [all data]

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McDiarmid, R., On the ultraviolet spectrum of trans-1,3-butadiene, J. Chem. Phys., 1976, 64, 514. [all data]

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Matthews and Warneck, 1969
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Eland, 1969
Eland, J.H.D., Photoelectron spectra of conjugated hydrocarbons and heteromolecules, Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 471. [all data]

Parr and Elder, 1968
Parr, A.C.; Elder, F.A., Photoionization of 1,3butadiene, 1,2-butadiene, allene, and propyne, J. Chem. Phys., 1968, 49, 2659. [all data]

Dewar and Worley, 1968
Dewar, M.J.S.; Worley, S.D., Ionization potential of cis-1,3-butadiene, J. Chem. Phys., 1968, 49, 2454. [all data]

Bock and Seidl, 1968
Bock, H.; Seidl, H., 'd-Orbital effects' in silicon- substituted π-electron systems. XI. Syntheses and properties of the isomeric bis(trimethylsilyl)-1,3-butadienes, J. Am. Chem. Soc., 1968, 90, 5694. [all data]

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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, Vibrational and/or electronic energy levels, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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