Phenylethyne

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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

Quantity Value Units Method Reference Comment
Δfgas73.27 ± 0.41kcal/molChydDavis, Allinger, et al., 1985ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
27.459298.15Evans J.C., 1960GT
27.629300.
35.949400.
42.670500.
48.009600.
52.290700.
55.791800.
58.709900.
61.1711000.
63.2601100.
65.0501200.
66.5801300.
67.9111400.
69.0511500.

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

Quantity Value Units Method Reference Comment
Δfliquid67.95 ± 0.96kcal/molCcbN/Arecalculated with modern CO2,H2O thermo; estimated uncertainty (NOTE all values in source also have wrong sign); DRB
Δfliquid-62.3kcal/molCcbMoureu and Andre, 1914ALS
Quantity Value Units Method Reference Comment
Δcliquid-1025.3kcal/molCcbMoureu and Andre, 1914Corresponding Δfliquid = 67.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid52.87cal/mol*KN/ALebedev, Bykova, et al., 1982DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
43.045298.15Lebedev, Bykova, et al., 1982T = 13.8 to 480 K.; DH
42.90298.5Smith and Andrews, 1931T = 102 to 298 K. Value is unsmoothed experimental datum.; DH

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

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 (kcal/mol) Temperature (K) Method Reference Comment
10.2 ± 0.02320.EBSteele, Chirico, et al., 2002Based on data from 313. to 416. K.; AC
9.66 ± 0.02360.EBSteele, Chirico, et al., 2002Based on data from 313. to 416. K.; AC
9.08 ± 0.05400.EBSteele, Chirico, et al., 2002Based on data from 313. to 416. K.; AC
10.5278.MMChickos, Hyman, et al., 1981Based on data from 265. to 291. K.; AC
10.8281.HSAChickos, Hyman, et al., 1981Based on data from 270. to 292. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.261228.04Lebedev, Bykova, et al., 1982DH
2.26228.Lebedev, Bykova, et al., 1982, 2AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
9.92228.04Lebedev, 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

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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:
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
Δr370.6 ± 2.3kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr362.9 ± 2.0kcal/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-66.12 ± 0.06kcal/molChydDavis, Allinger, et al., 1985liquid phase; solvent: Hexane; ALS
Δr-64.7 ± 0.9kcal/molChydRogers and McLafferty, 1971liquid phase; solvent: Hydrocarbon; ALS
Δr-70.7 ± 1.0kcal/molChydFlitcroft and Skinner, 1958liquid phase; ALS

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-3381
NIST MS number 228432

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UV/Visible 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Fihtengolts, et al., 1969
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 20171
Instrument SF-4
Boiling point 143

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

Fihtengolts, et al., 1969
Fihtengolts, V.S., et al., Atlas of UV Absorption Spectra of Substances Used in Synthetic Rubber Manufacture, 1969, 172. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References