Phenylethyne

• Formula: C₈H₆
• Molecular weight: 102.1332
• IUPAC Standard InChI: InChI=1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H Copy

  
• IUPAC Standard InChIKey: UEXCJVNBTNXOEH-UHFFFAOYSA-N Copy
• CAS Registry Number: 536-74-3
• 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:
  • Benzene, beta-deuteroethynyl-
  • Benzene, beta-deuteroethynyl-
• Other names: Benzene, ethynyl-; Ethyne, phenyl-; Ethynylbenzene; Phenylacetylene; 1-Phenylethyne; Acetylene, phenyl-; Ethinylbenzene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
• Options:
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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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of fusion

Entropy of fusion

Gas phase ion energetics data

Go To: Top, Phase change data, 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
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C₈H₆⁺ (ion structure unspecified)

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

De-protonation reactions

C₈H₅^- +  =

By formula: C₈H₅^- + H⁺ = C₈H₆

Gas Chromatography

Go To: Top, Phase change data, Gas phase ion energetics data, 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

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Kovats' RI, polar column, isothermal

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

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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Lee's RI, non-polar column, custom temperature program

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References

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes

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

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Smith, R.H.; Andrews, D.H., Thermal Energy Studies I. Phenyl Derivatives of Methane, Ethane and Some Related Compounds, J. Am. Chem. Soc., 1931, 53, 3644. [all data]

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Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Measurements of Vapor Pressure, Heat Capacity, and Density along the Saturation Line for γ-Caprolactam, Pyrazine, 1,2-Propanediol, Triethylene Glycol, Phenyl Acetylene, and Diphenyl Acetylene, J. Chem. Eng. Data, 2002, 47, 4, 689-699, https://doi.org/10.1021/je010085z . [all data]

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Chickos, James S.; Hyman, Arthur S.; Ladon, Liina H.; Liebman, Joel F., Measurement and estimation of the heats of vaporization of hydrocarbons, J. Org. Chem., 1981, 46, 21, 4294-4296, https://doi.org/10.1021/jo00334a040 . [all data]

Lebedev, Bykova, et al., 1982, 2
Lebedev, B.V.; Bykova, T.A.; Smirnova, N.N.; Kulagina, T.G., Thermodynmics of phenylacetylene, its cyclotrimerization, and the resulting 1,3,5-triphenylbenzene at 0-480 K, Zhur. Obshch. Khim., 1982, 52, 2630-2636. [all data]

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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]

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Dyke, Ozeki, et al., 1992
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Rabalais, J.W.; Colton, R.J., Electronic interaction between the phenyl group and its unsaturated substituents, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 83. [all data]

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Deshmukh, P.; Dutta, T.K.; Hwang, J.L.-S.; Housecroft, C.E.; Fehlner, T.P., Photoelectron spectroscopic measurements of the relative charge on carbyne fragments bound to polynuclear cobalt carbonyl clusters, J. Am. Chem. Soc., 1982, 104, 1740. [all data]

Palmer, Moyes, et al., 1980
Palmer, M.H.; Moyes, W.; Spiers, M., The electronic structure of substituted benzenes: Ab initio calculations and photoelectron spectra for benzonitrile, the tolunitriles, fluorobenzonitriles, dicyanobenzenes and ethynylbenzene, J. Mol. Struct., 1980, 62, 165. [all data]

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Griebel, Hohlneicher, et al., 1974
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Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Engewald, Topalova, et al., 1987
Engewald, W.; Topalova, I.; Petsev, N.; Dimitrov, Chr., Structure-Retention Correlations of Hydrocarbons in GLC and GSC. Alkenylbenzenes, Chromatographia, 1987, 23, 8, 561-565, https://doi.org/10.1007/BF02324864 . [all data]

Kugucheva and Mashinsky, 1983
Kugucheva, E.E.; Mashinsky, V.I., Retention Indices of Aromatic Hydrocarbons on Capillary Columns with Squalan and Polyphenyl Ether, Zh. Anal. Khim. (Rus), 1983, 38, 11, 2023-2026. [all data]

Tóth, 1983
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Rohrschneider, L., Eine methode zur charakterisierung von gaschromatographischen trennflüssigkeiten, J. Chromatogr., 1966, 22, 6-22, https://doi.org/10.1016/S0021-9673(01)97064-5 . [all data]

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Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization

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