1-Buten-3-yne

• Formula: C₄H₄
• Molecular weight: 52.0746
• IUPAC Standard InChI: InChI=1S/C4H4/c1-3-4-2/h1,4H,2H2 Copy

  
• IUPAC Standard InChIKey: WFYPICNXBKQZGB-UHFFFAOYSA-N Copy
• CAS Registry Number: 689-97-4
• 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: But-1-en-3-yne; Butenyne; Ethene, ethynyl-; Monovinylacetylene; Vinylacetylene; 1-Butene-3-yne; 1-Butyn-3-ene; 3-Buten-1-yne; Buten-3-yne; Ethynylethene; 1-Butenyne; Vinylethyne
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• Information on this page:
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry 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
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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:
L - Sharon G. Lias

Data compiled as indicated in comments:
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 C₄H₄⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

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

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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References

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

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

Rosenstock, McCulloh, et al., 1977
Rosenstock, H.M.; McCulloh, K.E.; Lossing, F.P., On the mechanisms of C₆H₆ ionization fragmentation, Int. J. Mass Spectrom. Ion Phys., 1977, 25, 327. [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]

Brogli, Heilbronner, et al., 1975
Brogli, F.; Heilbronner, E.; Wirz, J.; Kloster-Jensen, E.; Bergman, R.G.; Vollhardt, K.P.C.; Ashe, A.J., III, The consequences of σ and π conjugative interactions in mono-, di- and triacetylenes. A photoelectron spectroscopic investigation, Helv. Chim. Acta, 1975, 58, 2620. [all data]

Bruckmann and Klessinger, 1973
Bruckmann, P.; Klessinger, M., Photoelektronenspektren organischer verbindungen. III. Photoelektronenspektren acetylensubstituierter kleiner ringe, J. Electron Spectrosc. Relat. Phenom., 1973, 2, 341. [all data]

Li and McGee, 1969
Li, P.H.; McGee, H.A., Jr., Mass spectrum and ionization potential of condensed cyclobutadiene, Chem. Commun., 1969, 592. [all data]

Hedaya, Miller, et al., 1969
Hedaya, E.; Miller, R.D.; McNeil, D.W.; D'Angelo, P.F.; Schissel, P., Flash vacuum pyrolysis. V. Cyclobutadiene, J. Am. Chem. Soc., 1969, 91, 1875. [all data]

Varsel, Morrell, et al., 1960
Varsel, C.J.; Morrell, F.A.; Resnik, F.E.; Powell, W.A., Qualitative and quantitative analysis of organic compounds. Use of low-voltage mass spectrometry, Anal. Chem., 1960, 32, 182. [all data]

Polyakova, Zimina, et al., 1960
Polyakova, A.A.; Zimina, K.I.; Petrov, A.A.; Khmel'nitskii, R.A., Mass spectra of vinylalkylacetylenes, Zh. Obshch. Khim., 1960, 30, 912, In original 927. [all data]

Polyakova, Zimina, et al., 1959
Polyakova, A.A.; Zimina, K.I.; Petrov, A.A.; Klmel'nitskii, R.A., Mass Spectra and the structure of vinylacetylenes, Dokl. Phys. Chem., 1959, 127, 597, In original 386. [all data]

Van Hoorn, 1975
Van Hoorn, M.D., He(I) ionisation potentials and MO calculations of butenyne and the monomethyl-substituted butenynes, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 65. [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]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory, Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [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 ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy

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