Phenylethyne
- Formula: C8H6
- Molecular weight: 102.1332
- IUPAC Standard InChIKey: UEXCJVNBTNXOEH-UHFFFAOYSA-N
- 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:
- Other names: Benzene, ethynyl-; Ethyne, phenyl-; Ethynylbenzene; Phenylacetylene; 1-Phenylethyne; Acetylene, phenyl-; Ethinylbenzene
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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 |
---|---|---|---|---|---|
ΔfH°gas | 306.6 ± 1.7 | kJ/mol | Chyd | Davis, Allinger, et al., 1985 | ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
114.89 | 298.15 | Evans J.C., 1960 | GT |
115.60 | 300. | ||
150.41 | 400. | ||
178.53 | 500. | ||
200.87 | 600. | ||
218.78 | 700. | ||
233.43 | 800. | ||
245.64 | 900. | ||
255.94 | 1000. | ||
264.68 | 1100. | ||
272.17 | 1200. | ||
278.57 | 1300. | ||
284.14 | 1400. | ||
288.91 | 1500. |
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 |
---|---|---|---|---|---|
ΔfH°liquid | 284.3 ± 4.0 | kJ/mol | Ccb | N/A | recalculated with modern CO2,H2O thermo; estimated uncertainty (NOTE all values in source also have wrong sign); DRB |
ΔfH°liquid | -261. | kJ/mol | Ccb | Moureu and Andre, 1914 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -4289.9 | kJ/mol | Ccb | Moureu and Andre, 1914 | Corresponding ΔfHºliquid = 284. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 221.2 | J/mol*K | N/A | Lebedev, Bykova, et al., 1982 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
180.10 | 298.15 | Lebedev, Bykova, et al., 1982 | T = 13.8 to 480 K.; DH |
179.5 | 298.5 | Smith and Andrews, 1931 | T = 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 |
---|---|---|---|---|---|
Tboil | 415. to 417. | K | N/A | Farchan Laboratories, 1990 | BS |
Tboil | 416.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 415.65 | K | N/A | Smith and Andrews, 1931, 2 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tboil | 414.65 | K | N/A | Moureu and Andre, 1914, 2 | Uncertainty assigned by TRC = 3. K; TRC |
Tboil | 412.65 | K | N/A | Bruhl, 1886 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 228.35 | K | N/A | Smith and Andrews, 1931, 2 | Uncertainty assigned by TRC = 0.4 K; freezing point with theremocouple; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 228.04 | K | N/A | Lebedev, Bykova, et al., 1982, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
42.6 ± 0.1 | 320. | EB | Steele, Chirico, et al., 2002 | Based on data from 313. to 416. K.; AC |
40.4 ± 0.1 | 360. | EB | Steele, Chirico, et al., 2002 | Based on data from 313. to 416. K.; AC |
38.0 ± 0.2 | 400. | EB | Steele, Chirico, et al., 2002 | Based on data from 313. to 416. K.; AC |
43.9 | 278. | MM | Chickos, Hyman, et al., 1981 | Based on data from 265. to 291. K.; AC |
45.2 | 281. | HSA | Chickos, Hyman, et al., 1981 | Based on data from 270. to 292. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.460 | 228.04 | Lebedev, Bykova, et al., 1982 | DH |
9.46 | 228. | Lebedev, Bykova, et al., 1982, 2 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.5 | 228.04 | Lebedev, Bykova, et al., 1982 | DH |
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- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1551. ± 9.6 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1518. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: 2H2 + C8H6 = C8H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -276.6 ± 0.3 | kJ/mol | Chyd | Davis, Allinger, et al., 1985 | liquid phase; solvent: Hexane; ALS |
ΔrH° | -271. ± 4. | kJ/mol | Chyd | Rogers and McLafferty, 1971 | liquid phase; solvent: Hydrocarbon; ALS |
ΔrH° | -296. ± 4.2 | kJ/mol | Chyd | Flitcroft and Skinner, 1958 | liquid phase; ALS |
IR Spectrum
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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
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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