1,3-Butadiyne

• Formula: C₄H₂
• Molecular weight: 50.0587
• IUPAC Standard InChI: InChI=1S/C4H2/c1-3-4-2/h1-2H Copy

  
• IUPAC Standard InChIKey: LLCSWKVOHICRDD-UHFFFAOYSA-N Copy
• CAS Registry Number: 460-12-8
• 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.
• Isotopologues:
  • Butadiyne-d2
• Other names: Butadiyne; Biacetylene; Biethynyl; Diacetylene; HC≡CC≡CH; buta-1,3-diyne
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Electron-Impact Ionization Cross Sections (on physics web site)
  • Gas Phase Kinetics Database
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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

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

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of sublimation

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 by: John E. Bartmess

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

C₄H^- +  =

By formula: C₄H^- + H⁺ = C₄H₂

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

Data compiled as indicated in comments:
B - John E. Bartmess
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 C₄H₂⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H^- +  =

By formula: C₄H^- + H⁺ = C₄H₂

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

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:   D_∞h     Symmetry Number σ = 2

Source: Shimanouchi, 1972

Notes

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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.

Kiefer, Sidhu, et al., 1992
Kiefer, J.H.; Sidhu, S.S.; Kern, R.D.; Xie, K.; Chen, H.; Harding, L.B., The homogeneous pyrolysis of acetylene II: the high temperature radical chain mechanism, Combust. Sci. Technol., 1992, 82, 101-130. [all data]

Dorofeeva O.V., 1991
Dorofeeva O.V., Thermodynamic properties of linear carbon chain molecules with conjugated triple bonds. Part I. Polyacetylenes, H(CC)nH (n=2-6), cyanopolyacetylenes, H(CC)nCN (n=1-5), and dicyanopolyacetylenes, NC(CC)nCN (n=1-4), Thermochim. Acta, 1991, 178, 273-286. [all data]

Dessau L., 1988
Dessau L., Vibrations and thermodynamic functions of long-chain acetylenes, Z. Phys. Chem. (Leipzig), 1988, 269, 187-190. [all data]

Pauling, Springall, et al., 1939
Pauling, L.; Springall, H.D.; Palmer, K.J., The Electron Diffraction Investigation of Methylacetylene, Dimethyl- acetylene, Dimethyldiacetylene, Methyl Cyanide, Diacetylene and Cyanogen cyanogen, J. Am. Chem. Soc., 1939, 61, 927-8. [all data]

Straus and Kollek, 1926
Straus, F.; Kollek, L., About Diacetylene, Ber. Dtsch. Chem. Ges., 1926, 59, 1664-81. [all data]

Mueller, 1925
Mueller, F.G., Diacetylene (1,3-butadiyne), Helv. Chim. Acta, 1925, 8, 826-32. [all data]

Straus and Kollek, 2006
Straus, Fritz; Kollek, Leo, Über Diacetylen, Ber. dtsch. Chem. Ges. A/B, 2006, 59, 8, 1664-1681, https://doi.org/10.1002/cber.19260590804 . [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]

Tanneberger, 2006
Tanneberger, H., Einige Bemerkungen über die Dampfdruck-Kurve des Diacetylens (Butadiins)., Ber. dtsch. Chem. Ges. A/B, 2006, 66, 4, 484-486, https://doi.org/10.1002/cber.19330660408 . [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]

Dykyj, 1971
Dykyj, J., Petrochemia, 1971, 11, 2, 27. [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Straus and Kollek, 1926, 2
Straus, F.; Kollek, L., Uber Diacetylen, Ber. Dtsch. Chem. Ges., 1926, 59, 8, 1664-1681, https://doi.org/10.1002/cber.19260590804 . [all data]

Pino, Tulej, et al., 2002
Pino, T.; Tulej, M.; Guthe, F.; Pachkov, M.; Maier, J.P., Photodetachment spectroscopy of the C2nH- (n=2-4) anions in the vicinity of their electron detachment threshold, J. Chem. Phys., 2002, 116, 14, 6126-6131, https://doi.org/10.1063/1.1451248 . [all data]

Shi and Ervin, 2000
Shi, Y.; Ervin, K.M., Gas-phase acidity and C-H bond energy of diacetylene, Chem. Phys. Lett., 2000, 318, 1-3, 149-154, https://doi.org/10.1016/S0009-2614(00)00023-3 . [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]

Bieri, Schmelzer, et al., 1980
Bieri, G.; Schmelzer, A.; Asbrink, L.; Jonsson, M., Fluorine and the fluoroderivatives of acetylene and diacetylene studied by 30.4 nm He(II) photoelectron spectroscopy, Chem. Phys., 1980, 49, 213. [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]

Reeher, Flesch, et al., 1976
Reeher, J.R.; Flesch, G.D.; Svec, H.J., The mass spectra and ionization potentials of the neutral fragments produced during the electron bombardment of aromatic compounds, Org. Mass Spectrom., 1976, 11, 154. [all data]

Brogli, Heilbronner, et al., 1973
Brogli, F.; Heilbronner, E.; Hornung, V.; Kloster-Jensen, E., 230. Die photoelektronen-spektren methyl-substituierter Acetylene, Helv. Chim. Acta, 1973, 56, 2171. [all data]

Smith, 1967
Smith, W.L., The absorption spectrum of diacetylene in the vacuum ultraviolet, Proc. Roy. Soc. (London), 1967, A300, 519. [all data]

Baker and Turner, Commun. 1967
Baker, C.; Turner, D.W., Photoelectron spectra of acetylene, diacetylene, and their deutero-derivatives, Chem., Commun. 1967, 797. [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]

Coats and Anderson, 1957
Coats, F.H.; Anderson, R.C., Thermodynamic data from electron-impact measurements on acetylene and substituted acetylenes, J. Am. Chem. Soc., 1957, 79, 1340. [all data]

Fihtengolts, et al., 1969
Fihtengolts, V.S., et al., Atlas of UV Absorption Spectra of Substances Used in Synthetic Rubber Manufacture, 1969, 172. [all data]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization

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