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
- 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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
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, 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 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 | 73.27 ± 0.41 | kcal/mol | Chyd | Davis, Allinger, et al., 1985 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 27.459 | 298.15 | Evans J.C., 1960 | GT |
| 27.629 | 300. | ||
| 35.949 | 400. | ||
| 42.670 | 500. | ||
| 48.009 | 600. | ||
| 52.290 | 700. | ||
| 55.791 | 800. | ||
| 58.709 | 900. | ||
| 61.171 | 1000. | ||
| 63.260 | 1100. | ||
| 65.050 | 1200. | ||
| 66.580 | 1300. | ||
| 67.911 | 1400. | ||
| 69.051 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry 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 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 | 67.95 ± 0.96 | kcal/mol | Ccb | N/A | recalculated with modern CO2,H2O thermo; estimated uncertainty (NOTE all values in source also have wrong sign); DRB |
| ΔfH°liquid | -62.3 | kcal/mol | Ccb | Moureu and Andre, 1914 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1025.3 | kcal/mol | Ccb | Moureu and Andre, 1914 | Corresponding ΔfHºliquid = 67.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 52.87 | cal/mol*K | N/A | Lebedev, Bykova, et al., 1982 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 43.045 | 298.15 | Lebedev, Bykova, et al., 1982 | T = 13.8 to 480 K.; DH |
| 42.90 | 298.5 | Smith and Andrews, 1931 | T = 102 to 298 K. Value is unsmoothed experimental datum.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 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° | 370.6 ± 2.3 | kcal/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° | 362.9 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
2 +
=
By formula: 2H2 + C8H6 = C8H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -66.12 ± 0.06 | kcal/mol | Chyd | Davis, Allinger, et al., 1985 | liquid phase; solvent: Hexane; ALS |
| ΔrH° | -64.7 ± 0.9 | kcal/mol | Chyd | Rogers and McLafferty, 1971 | liquid phase; solvent: Hydrocarbon; ALS |
| ΔrH° | -70.7 ± 1.0 | kcal/mol | Chyd | Flitcroft and Skinner, 1958 | liquid phase; ALS |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, 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]
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, Reaction thermochemistry data, 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 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.