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
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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Electron-Impact Ionization Cross Sections (on physics web site)
  • Gas Phase Kinetics Database
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Phase change data

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
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

Gas phase ion energetics data

Go To: Top, Phase change data, Mass spectrum (electron ionization), References, Notes

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

Mass spectrum (electron ionization)

Go To: Top, Phase change data, Gas phase ion energetics 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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
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
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

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]

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]

Dannacher, Flamme, et al., 1980
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]

Bieri and Asbrink, 1980
Bieri, G.; Asbrink, L., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1980, 20, 149. [all data]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

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

Brundle and Robin, 1970
Brundle, C.R.; Robin, M.B., Nonplanarity in hexafluorobutadiene as revealed by photoelectron and optical spectroscopy, J. Am. Chem. Soc., 1970, 92, 5550. [all data]

Matthews and Warneck, 1969
Matthews, C.S.; Warneck, P., Heats of formation of CHO⁺ and C₃H₃⁺ by photoionization, J. Chem. Phys. 5, 1969, 1, 854. [all data]

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]

Franklin and Mogenis, 1967
Franklin, J.L.; Mogenis, A., An electron impact study of ions from several dienes, J. Phys. Chem., 1967, 71, 2820. [all data]

Brehm, 1966
Brehm, B., Massenspektrometrische Untersuchung der Photoionisation von Molekulen, Z. Naturforsch., 1966, 21a, 196. [all data]

Watanabe, 1954
Watanabe, K., Photoionization and total absorption cross section of gases. I. Ionization potentials of several molecules. Cross sections of NH₃ and NO, J. Chem. Phys., 1954, 22, 1564. [all data]

Price and Walsh, 1940
Price, W.C.; Walsh, A.D., The absorption spectra of conjugated dienes in the vacuum ultra-violet (1), Proc. Roy. Soc. (London), 1940, A174, 220. [all data]

Schmidt, Schweig, et al., 1976
Schmidt, H.; Schweig, A.; Anastassiou, A.G.; Wetzel, J.C., The dominant role of hyperconjugation in the 9-oxabicyclo[4.2.1]nona-2,4,7-triene series, Tetrahedron, 1976, 32, 2239. [all data]

Field, Franklin, et al., 1957
Field, F.H.; Franklin, J.L.; Lampe, F.W., Reactions of gaseous ions. II. Acetylene, J. Am. Chem. Soc., 1957, 79, 2665. [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]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  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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