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
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Phase change data
  • Henry's Law data
• 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
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, 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: 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

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, 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

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)

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, 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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

Vibrational and/or electronic energy levels

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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: Takehiko Shimanouchi

Symmetry:   D_∞h     Symmetry Number σ = 2

Source: Shimanouchi, 1972

Notes

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, 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

Kovats' RI, non-polar column, isothermal

View large format table.

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Normal alkane RI, non-polar column, temperature ramp

View large format table.

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, 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]

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]

Do and Raulin, 1992
Do, L.; Raulin, F., Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column, J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R . [all data]

Kaiser and Siegl, 1994
Kaiser, E.W.; Siegl, W.O., High resolution gas chromatographic determination of the atmospheric reactivity of engine-out hydrocarbon emissions from a spark-ignited engine, J. Hi. Res. Chromatogr., 1994, 17, 4, 264-270, https://doi.org/10.1002/jhrc.1240170414 . [all data]

Bramston-Cook, 2013
Bramston-Cook, R., Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  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

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.