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:
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • 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
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Condensed 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

• GAS (VAPOR PRESSURE OF LIQUID AT ROOM TEMPERATURE); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• GAS (VAPOR PRESSURE OF LIQUID AT ROOM TEMPERATURE) $$ SEE SPECTRUM NO. 10136 FOR "SOLUTION" STATE $$ SEE SP. ACTA, VOL. 16, P. 918, 1960; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm^-1 resolution
• SOLUTION (10% CCl4 FOR 2.5-7.5, 10% CS2 FOR 7.5-15 MICRON); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 3800-1333, 10% IN CS2 FOR 1333-450 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas

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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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, Condensed phase thermochemistry data, IR Spectrum, Gas Chromatography, Notes

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

Moureu and Andre, 1914
Moureu, C.; Andre, E., Thermochimie des composes acetyleniques, Ann. Chim. Phys., 1914, 1, 113-145. [all data]

Lebedev, Bykova, et al., 1982
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]

Smith and Andrews, 1931
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, 3644-3660. [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
Tóth, T., Use of capillary gas chromatography in collecting retention and chemical information for the analysis of complex petrochemical mixtures, J. Chromatogr., 1983, 279, 157-165, https://doi.org/10.1016/S0021-9673(01)93614-3 . [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

Macák, Nabivach, et al., 1982
Macák, J.; Nabivach, V.; Buryan, P.; Sindler, S., Dependence of retention indices of alkylbenzenes on their molecular structure, J. Chromatogr., 1982, 234, 2, 285-302, https://doi.org/10.1016/S0021-9673(00)81867-1 . [all data]

Nabivach, Bur'yan, et al., 1978
Nabivach, V.M.; Bur'yan, P.; Matsak, I., Retention indices of aromatic hydrocarbons on a squalane capillary column, Zh. Anal. Khim., 1978, 33, 7, 1108-1113. [all data]

Rohrschneider, 1966
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]

Xu, van Stee, et al., 2003
Xu, X.; van Stee, L.L.P.; Williams, J.; Beens, J.; Adahchour, M.; Vreuls, R.J.J.; Brinkman, U.A.Th.; Lelieveld, J., Comprehensive two-dimensional gas chromatography (GC×GC) measurements of volatile organic compounds in the atmosphere, Atmos. Chem. Phys., 2003, 3, 3, 665-682, https://doi.org/10.5194/acp-3-665-2003 . [all data]

Dallüge, van Stee, et al., 2002
Dallüge, J.; van Stee, L.L.P.; Xu, X.; Williams, J.; Beens, J.; Vreuls, R.J.J.; Brinkman, U.A.Th., Unravelling the composition of very complex samples by comprehensive gas chromatography coupled to time-of-flight mass spectrometry. Cigarette smoke, J. Chromatogr. A, 2002, 974, 1-2, 169-184, https://doi.org/10.1016/S0021-9673(02)01384-5 . [all data]

Helmig, Pollock, et al., 1996
Helmig, D.; Pollock, W.; Greenberg, J.; Zimmerman, P., Gas chromatography mass spectrometry analysis of volatile organic trace gases at Mauna Loa Observatory, Hawaii, J. Geophys. Res., 1996, 101, D9, 14697-14710, https://doi.org/10.1029/96JD00212 . [all data]

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

Guan, Zheng, et al., 1992
Guan, Y.; Zheng, P.; Zhou, L., Prediction, optimization of separation, and identification of unknown compounds in capillary gas chromatography, J. Hi. Res. Chromatogr., 1992, 15, 1, 18-23, https://doi.org/10.1002/jhrc.1240150106 . [all data]

Tirillini, Verdelli, et al., 2000
Tirillini, B.; Verdelli, G.; Paolocci, F.; Ciccioli, P.; Frattoni, M., The volatile organic compounds from the mycelium of Tuber borchii Vitt., Phytochemistry, 2000, 55, 8, 983-985, https://doi.org/10.1016/S0031-9422(00)00308-3 . [all data]

Zenkevich and Kuznetsova, 1990
Zenkevich, I.G.; Kuznetsova, L.M., Logic Criteria on Prediction of Gas Chromatographic Retention Indices from Physico-Chemical Properties of Organic Compounds, Dokl. Akad. Nauk SSSR, 1990, 315, 4, 881-885. [all data]

Soria, Sanz, et al., 2008
Soria, A.C.; Sanz, J.; Martinez-Castro, I., SPME followed by GC-MS: a powerful technique for qualitative analysis of honey volatiles, Eur. Food Res. Technol., 2008, 1-12. [all data]

de la Fuente, Martinez-Castro, et al., 2005
de la Fuente, E.; Martinez-Castro, I.; Sanz, J., Characterization of Spanish unifloral honeys by solid phase microextraction and gas chromatography-mass spectrometry, J. Sep. Sci., 2005, 28, 9-10, 1093-1100, https://doi.org/10.1002/jssc.200500018 . [all data]

Soria, Gonzalez, et al., 2004
Soria, A.C.; Gonzalez, M.; de Lorenzo, C.; Martinez-Castro, I.; Sanza, J., Characterization of artisanal honeys from Madrid (Central Spain) on the basis of their melissopalynological, physicochemical and volatile composition data, Food Chem., 2004, 85, 1, 121-130, https://doi.org/10.1016/j.foodchem.2003.06.012 . [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Wang, Hou, et al., 2007
Wang, G.; Hou, Z.; Sun, Y.; Liu, Y.; Xie, B.; Liu, S., Investigation of pyrolysis behavior of fenoxycarb using PY-GC-MS assisted with chemometric methods, Chem. Anal., 2007, 52, 141-156. [all data]

Shao, Wang, et al., 2006
Shao, X.; Wang, G.; Sun, Y.; Zhang, R.; Xie, K.; Liu, H., Determination and Characterization of the Pyrolysis Products of Isoprocarb by GC-MS, J. Chromatogr. Sci., 2006, 44, 3, 141-147, https://doi.org/10.1093/chromsci/44.3.141 . [all data]

Aracil, Font, et al., 2005
Aracil, I.; Font, R.; Conesa, J.A., Semivolatile and volatile compounds from the pyrolysis and combustion of polyvinyl chloride, J. Anal. Appl. Pyrolysis, 2005, 74, 1-2, 465-478, https://doi.org/10.1016/j.jaap.2004.09.008 . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, IR Spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions

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