3-Hexyne

• Formula: C₆H₁₀
• Molecular weight: 82.1436
• IUPAC Standard InChI: InChI=1S/C6H10/c1-3-5-6-4-2/h3-4H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: DQQNMIPXXNPGCV-UHFFFAOYSA-N Copy
• CAS Registry Number: 928-49-4
• 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: Diethylacetylene; C2H5C≡CC2H5; Hex-3-yne
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Antoine Equation Parameters

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

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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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₆H₁₀⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

References

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

Rogers, Dagdagan, et al., 1979
Rogers, D.W.; Dagdagan, O.A.; Allinger, N.L., Heats of hydrogenation and formation of linear alkynes and a molecular mechanics interpretation, J. Am. Chem. Soc., 1979, 101, 671-676. [all data]

Rondeau and Harrah, 1965
Rondeau, R.E.; Harrah, L.A., Melting Point and Vapor Pressures of 3-Hexyne, J. Chem. Eng. Data, 1965, 10, 84-5. [all data]

Pomerantz, Fookson, et al., 1954
Pomerantz, P.; Fookson, A.; Mears, T.W.; Rothberg, S.; Howard, F.L., Synthesis and Physical Properties of Several Acetylenic Hydrocarbons, J. Res. Natl. Bur. Stand. (U. S.), 1954, 52, 51. [all data]

Henne and Greenlee, 1945
Henne, A.L.; Greenlee, K.W., Preparation and Physical Constants of Acetylenic Compounds, J. Am. Chem. Soc., 1945, 67, 484-5. [all data]

Campbell and Eby, 1941
Campbell, K.N.; Eby, L.T., The Reduction of Multiple Carbon-Carbon Bonds III. Further Studies on the Preparation of Olefins from Acetylenes, J. Am. Chem. Soc., 1941, 63, 2683. [all data]

Rondeau and Harrah, 1965, 2
Rondeau, R.E.; Harrah, L.A., Melting Point and Vapor Pressures of 3-Hexyne., J. Chem. Eng. Data, 1965, 10, 1, 84-85, https://doi.org/10.1021/je60024a031 . [all data]

Wolkoff, Holmes, et al., 1980
Wolkoff, P.; Holmes, J.L.; Lossing, F.P., On the formation of cyclopentenium cations from all C₆H₁₀⁺ molecular ion structures, Can. J. Chem., 1980, 58, 251. [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]

Carlier, Dubois, et al., 1975
Carlier, P.; Dubois, J.E.; Masclet, P.; Mouvier, G., Spectres de photoelectrons des alcynes, J. Electron Spectrosc. Relat. Phenom., 1975, 7, 55. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions

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