2-Hexyne

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

  
• IUPAC Standard InChIKey: MELUCTCJOARQQG-UHFFFAOYSA-N Copy
• CAS Registry Number: 764-35-2
• 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: Methyl(propyl)acetylene; 1-Methyl-2-propylacetylene; C3H7C≡CCH3; Hex-2-yne
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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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

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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

2 +  =

By formula: 2H₂ + C₆H₁₀ = C₆H₁₄

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
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 C₆H₁₀⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

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

Gas Phase Spectrum

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Additional Data

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, polar column, isothermal

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes

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]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [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]

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]

Boukais-Belaribi, Belaribi, et al., 2007
Boukais-Belaribi, Ghénima; Belaribi, Brahim Farid; Lohmann, Juergën; Jose, Jacques, Isothermal vapour--liquid equilibria and excess molar enthalpies of hex-2-yne+methyl butyl ether and hex-3-yne+dibutyl ether mixtures, Fluid Phase Equilibria, 2007, 262, 1-2, 180-186, https://doi.org/10.1016/j.fluid.2007.09.002 . [all data]

Boukais-Belaribi, Belaribi, et al., 2006
Boukais-Belaribi, Ghénima; Belaribi, Brahim Farid; Ait-Kaci, Ahmed; Jose, Jacques, Thermodynamics of isomeric hexynes+MTBE binary mixtures, Fluid Phase Equilibria, 2006, 248, 2, 181-190, https://doi.org/10.1016/j.fluid.2006.08.007 . [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]

Rondeau and Harrah, 1965
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]

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]

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]

Praet, 1970
Praet, M.-Th., Ionisation et dissociation du 1-methyl-cyclopentene, du methylenecyclopentane et de quelques isomeres par impact d'electrons et de photons, Org. Mass Spectrom., 1970, 4, 65. [all data]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

Soják, Farkas, et al., 1991
Soják, L.; Farkas, P.; Ostrovský, I.; Janák, J.; Chrétien, J.R., Capillary gas chromatography of C₅ - C₁₃ branched alkynes on squalane and liquid crystal stationary phases, J. Chromatogr., 1991, 557, 241-253, https://doi.org/10.1016/S0021-9673(01)87136-3 . [all data]

Rang, Kuningas, et al., 1976
Rang, S.; Kuningas, K.; Orav, A.; Eisen, O., Capillary gas chromatography of n-alkynes. I. Retention indices, J. Chromatogr., 1976, 119, 451-460, https://doi.org/10.1016/S0021-9673(00)86807-7 . [all data]

Orav and Eisen, 1972
Orav, A.; Eisen, O., The retention indexes for alkenes, alkynes and cyclenes on capillary columns, Izv. Akad. Nauk Est. SSR, Khim. Geol., 1972, 21, 1, 39-47. [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]

Rang, Orav, et al., 1988
Rang, S.A.; Orav, A.E.; Kuningas, K.R.; Meister, A.E.; Strense, T.V.; Eisen, O.G., Gas-Chromatographic Characteristics of unsaturated hydrocarbons, Academy of Sciences of Estonia SSR, Tallinn, Estonia SSR, 1988, 208. [all data]

Zenkevich and Marinichev, 2001
Zenkevich, I.G.; Marinichev, A.N., Comparison of Topological and Dynamics Molecular Characteristics for Precalculation of Chromatographic Retention Parameters of Organic Compounds (in Russian), Zh. Struct. Khim., 2001, 42, 5, 893-902. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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