Phenylethyne

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas306.6 ± 1.7kJ/molChydDavis, Allinger, et al., 1985ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
114.89298.15Evans J.C., 1960GT
115.60300.
150.41400.
178.53500.
200.87600.
218.78700.
233.43800.
245.64900.
255.941000.
264.681100.
272.171200.
278.571300.
284.141400.
288.911500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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 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

Quantity Value Units Method Reference Comment
Δfliquid284.3 ± 4.0kJ/molCcbN/Arecalculated with modern CO2,H2O thermo; estimated uncertainty (NOTE all values in source also have wrong sign); DRB
Δfliquid-261.kJ/molCcbMoureu and Andre, 1914ALS
Quantity Value Units Method Reference Comment
Δcliquid-4289.9kJ/molCcbMoureu and Andre, 1914Corresponding Δfliquid = 284. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid221.2J/mol*KN/ALebedev, Bykova, et al., 1982DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
180.10298.15Lebedev, Bykova, et al., 1982T = 13.8 to 480 K.; DH
179.5298.5Smith and Andrews, 1931T = 102 to 298 K. Value is unsmoothed experimental datum.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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 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

Quantity Value Units Method Reference Comment
Tboil415. to 417.KN/AFarchan Laboratories, 1990BS
Tboil416.2KN/AWeast and Grasselli, 1989BS
Tboil415.65KN/ASmith and Andrews, 1931, 2Uncertainty assigned by TRC = 1.5 K; TRC
Tboil414.65KN/AMoureu and Andre, 1914, 2Uncertainty assigned by TRC = 3. K; TRC
Tboil412.65KN/ABruhl, 1886Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus228.35KN/ASmith and Andrews, 1931, 2Uncertainty assigned by TRC = 0.4 K; freezing point with theremocouple; TRC
Quantity Value Units Method Reference Comment
Ttriple228.04KN/ALebedev, Bykova, et al., 1982, 2Uncertainty assigned by TRC = 0.02 K; TRC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
42.6 ± 0.1320.EBSteele, Chirico, et al., 2002Based on data from 313. to 416. K.; AC
40.4 ± 0.1360.EBSteele, Chirico, et al., 2002Based on data from 313. to 416. K.; AC
38.0 ± 0.2400.EBSteele, Chirico, et al., 2002Based on data from 313. to 416. K.; AC
43.9278.MMChickos, Hyman, et al., 1981Based on data from 265. to 291. K.; AC
45.2281.HSAChickos, Hyman, et al., 1981Based on data from 270. to 292. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
9.460228.04Lebedev, Bykova, et al., 1982DH
9.46228.Lebedev, Bykova, et al., 1982, 2AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
41.5228.04Lebedev, Bykova, et al., 1982DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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 compiled as indicated in comments:
B - John E. Bartmess
ALS - 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

C8H5- + Hydrogen cation = Phenylethyne

By formula: C8H5- + H+ = C8H6

Quantity Value Units Method Reference Comment
Δr1551. ± 9.6kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1518. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

2Hydrogen + Phenylethyne = Ethylbenzene

By formula: 2H2 + C8H6 = C8H10

Quantity Value Units Method Reference Comment
Δr-276.6 ± 0.3kJ/molChydDavis, Allinger, et al., 1985liquid phase; solvent: Hexane; ALS
Δr-271. ± 4.kJ/molChydRogers and McLafferty, 1971liquid phase; solvent: Hydrocarbon; ALS
Δr-296. ± 4.2kJ/molChydFlitcroft and Skinner, 1958liquid phase; ALS

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-101100.870.Engewald, Topalova, et al., 1987Column length: 50. m; Column diameter: 0.30 mm
CapillarySqualane106.833.Kugucheva and Mashinsky, 1983He; Column length: 100. m
CapillarySqualane96.830.Kugucheva and Mashinsky, 1983He; Column length: 100. m
CapillarySE-3070.862.1Tóth, 1983N2; Column length: 15. m; Column diameter: 0.25 mm
CapillarySE-30130.875.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySE-3080.862.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySqualane86.830.4Macák, Nabivach, et al., 1982N2; Column length: 50. m; Column diameter: 0.25 mm
CapillarySqualane96.834.1Macák, Nabivach, et al., 1982N2; Column length: 50. m; Column diameter: 0.25 mm
CapillarySqualane86.830.4Nabivach, Bur'yan, et al., 1978Column length: 50. m; Column diameter: 0.25 mm
CapillarySqualane96.834.1Nabivach, Bur'yan, et al., 1978Column length: 50. m; Column diameter: 0.25 mm
PackedDC-200100.868.Rohrschneider, 1966Column length: 4. m
PackedSqualane100.833.Rohrschneider, 1966Column length: 5. m
PackedApiezon L100.875.Rohrschneider, 1966Column length: 5. m

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryPEG-20M70.1357.2Tóth, 1983N2; Column length: 30. m; Column diameter: 0.3 mm
PackedCarbowax 20M100.1370.Rohrschneider, 1966Column length: 2. m

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

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-5881.0Xu, van Stee, et al., 200330. m/0.25 mm/1. μm, He, 2.5 K/min; Tstart: 50. C; Tend: 200. C
CapillaryDB-5877.Dallüge, van Stee, et al., 200230. m/0.25 mm/1. μm, He, 2.5 K/min; Tstart: 50. C; Tend: 200. C
CapillaryDB-5875.9Helmig, Pollock, et al., 199660. m/0.33 mm/0.25 μm, 6. K/min; Tstart: -50. C; Tend: 180. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryOV-101856.Zenkevich, 200525. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C
CapillaryOV-1849.Guan, Zheng, et al., 199250. m/0.32 mm/0.52 μm, H2, 1. K/min; Tstart: 30. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryCP-Sil5 CB MS863.Tirillini, Verdelli, et al., 200050. m/0.32 mm/0.4 μm; Program: 0C (3min) => 3C/min => 50C => 5C/min => 220C (30min)
CapillaryMethyl Silicone862.Zenkevich and Kuznetsova, 1990Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-Innowax1372.Soria, Sanz, et al., 200850. m/0.20 mm/0.20 μm, Helium, 45. C @ 2. min, 4. K/min, 190. C @ 50. min
CapillaryCarbowax 20M1354.de la Fuente, Martinez-Castro, et al., 200550. m/0.25 mm/0.25 μm, Helium, 40. C @ 2. min, 4. K/min, 190. C @ 30. min
CapillaryHP-Innowax1372.Soria, Gonzalez, et al., 200450. m/0.2 mm/0.2 μm, He, 45. C @ 2. min, 4. K/min, 190. C @ 50. min

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1361.Peng, Yang, et al., 1991Program: not specified

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

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5122.0Wang, Hou, et al., 200730. m/0.30 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 200. C @ 15. min
CapillaryHP-5122.1Shao, Wang, et al., 200630. m/0.3 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min, 200. C @ 15. min

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

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-5MS122.7Aracil, Font, et al., 2005Column length: 60. m; Column diameter: 0.25 mm; Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, Notes

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

Davis, Allinger, et al., 1985
Davis, H.E.; Allinger, N.L.; Rogers, D.W., Enthalpies of hydrogenation of phenylalkynes: indirect determination of the enthalpy of formation of diphenylcyclopropenone, J. Org. Chem., 1985, 50, 3601-3604. [all data]

Evans J.C., 1960
Evans J.C., The vibrational spectra ethynyl benzene and ethynyl benzene-d, Spectrochim. Acta, 1960, 16, 918-928. [all data]

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]

Farchan Laboratories, 1990
Farchan Laboratories, Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Smith and Andrews, 1931, 2
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]

Moureu and Andre, 1914, 2
Moureu, C.; Andre, E., Thermochemistry of Acetylenic Compounds, Ann. Chim. (Paris), 1914, 1, 113. [all data]

Bruhl, 1886
Bruhl, J.W., Investigation of Molar Refraction of ORganic Liquids from Light Scattering Measurements, Justus Liebigs Ann. Chem., 1886, 235, 1. [all data]

Lebedev, Bykova, et al., 1982, 2
Lebedev, B.V.; Bykova, T.A.; Smirnova, N.N.; Kulagina, T.G., Zh. Obshch. Khim., 1982, 52, 2630. [all data]

Steele, Chirico, et al., 2002
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]

Chickos, Hyman, et al., 1981
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]

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]

Rogers and McLafferty, 1971
Rogers, D.W.; McLafferty, F.J., A new hydrogen calorimeter. Heats of hydrogenation of allyl and vinyl unsaturation adjacent to a ring, Tetrahedron, 1971, 27, 3765-3775. [all data]

Flitcroft and Skinner, 1958
Flitcroft, T.L.; Skinner, H.A., Heats of hydrogenation Part 2.-Acetylene derivatives, Trans. Faraday Soc., 1958, 54, 47-53. [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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References