Diphenylacetylene
- Formula: C14H10
- Molecular weight: 178.2292
- IUPAC Standard InChIKey: JRXXLCKWQFKACW-UHFFFAOYSA-N
- CAS Registry Number: 501-65-5
- 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. - Other names: Diphenylethyne; Benzene, 1,1'-(1,2-ethynediyl)bis-; Acetylene, diphenyl-; Ethyne, diphenyl-; Tolan; Tolane; 1,2-Diphenylacetylene; 1,1'-(1,2-Ethanediyl)bisbenzene; NSC 5185
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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 | 385. ± 2.7 | kJ/mol | Chyd | Davis, Allinger, et al., 1985 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 452. | J/mol*K | N/A | Alcolea Palafox M., 1996 | This value was calculated by semiempirical AM1 method. According to estimation by difference method [ Dorofeeva O.V., 1997] it could be overestimated by 15-30 J/mol*K.; GT |
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 by: 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
By formula: C15H10O = C14H10 + CO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28. ± 5.0 | kJ/mol | Cpha | Hung and Grabowski, 1992 | liquid phase; solvent: Alkane |
ΔrH° | 18. ± 10. | kJ/mol | Cpha | Herman and Goodman, 1989 | solid phase; solvent: Acetonitrile/water |
ΔrH° | -41. ± 12. | kJ/mol | Cpha | Grabowski, Simon, et al., 1984 | liquid phase; solvent: Benzene |
By formula: 2H2 + C14H10 = C14H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -249.5 ± 2.3 | kJ/mol | Chyd | Davis, Allinger, et al., 1985 | liquid phase; solvent: Hexane |
ΔrH° | -268.6 ± 4.6 | kJ/mol | Chyd | Flitcroft and Skinner, 1958 | solid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -268. ± 4.6 kJ/mol |
Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
View reactions leading to C14H10+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.94 ± 0.03 | eV | N/A | N/A | L |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
<0.321 ± 0.074 | ECD | Wojnarovits and Foldiak, 1981 | G3MP2B3 calculations indicate an EA of ca. 0.2 eV; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.95 ± 0.08 | PE | Elbel, Lienert, et al., 1981 | LLK |
7.90 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
8.0 ± 0.05 | PE | Eland, 1972 | LLK |
7.91 | PE | Rowland, 1971 | Unpublished result of J.H.D. Eland; LLK |
23.4 ± 0.1 | EI | Natalis and Franklin, 1965 | RDSH |
8.85 ± 0.05 | EI | Natalis and Franklin, 1965 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H5+ | 20.7 ± 0.1 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C8H6+ | 17.8 ± 0.1 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C9H5+ | 21.3 ± 0.2 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C9H7+ | 17.5 ± 0.1 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C10H6+ | 18.2 ± 0.1 | 2C2H2 | EI | Natalis and Franklin, 1965 | RDSH |
C11H7+ | 17.5 ± 0.1 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C12H7+ | 17.46 ± 0.06 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C12H8+ | 15.58 ± 0.05 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C12H82+ | 20.5 ± 0.1 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C14H8+ | 16.66 ± 0.05 | H2 | EI | Natalis and Franklin, 1965 | RDSH |
C14H9+ | 15.1 ± 0.1 | H | EI | Natalis and Franklin, 1965 | RDSH |
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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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-2603 |
NIST MS number | 228985 |
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, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | missing citation |
---|---|
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. 9001 |
Instrument | Perkin Elmer 350 |
Melting point | 62.5 |
Boiling point | 300 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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]
Alcolea Palafox M., 1996
Alcolea Palafox M.,
Vibrational spectra and structure of diphenylacetylenes,
Spectrosc. Lett., 1996, 29, 241-266. [all data]
Dorofeeva O.V., 1997
Dorofeeva O.V.,
Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]
Hung and Grabowski, 1992
Hung, R.R.; Grabowski, J.J.,
Enthalpy measurements in organic solvents by photoacoustic calorimetry: a solution to the reaction volume problem,
J. Am. Chem. Soc., 1992, 114, 351-353. [all data]
Herman and Goodman, 1989
Herman, M.S.; Goodman, J.L.,
Determination of the enthalpy and reaction volume changes of organic photoreactions using photoacoustic calorimetry,
J. Am. Chem. Soc., 1989, 111, 1849-1854. [all data]
Grabowski, Simon, et al., 1984
Grabowski, J.J.; Simon, J.D.; Peters, K.S.,
Heat of formation of diphenylcyclopropenone by photoacoustic calorimetry,
J. Am. Chem. Soc., 1984, 106, 4615-4616. [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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G.,
Electron capture detection of aromatic hydrocarbons,
J. Chromatogr. Sci., 1981, 206, 511. [all data]
Elbel, Lienert, et al., 1981
Elbel, S.; Lienert, K.; Krebs, A.; tom Dieck, H.,
Phenylethin - mustersonde fur substituenteneffekte,
Liebigs Ann. Chem., 1981, 1785. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]
Eland, 1972
Eland, J.H.D.,
Photoelectron spectra and ionization potentials of aromatic hydrocarbons,
Int. J. Mass Spectrom. Ion Phys., 1972, 9, 214. [all data]
Rowland, 1971
Rowland, C.G.,
Kinetic energy distributions of C12H8 fragment ions in the mass spectra of anthracene, phenanthrene and diphenylacetylene,
Intern. J. Mass Spectrom. Ion Phys., 1971, 7, 79. [all data]
Natalis and Franklin, 1965
Natalis, P.; Franklin, J.L.,
Ionization and dissociation of diphenyl and condensed ring aromatics by electron impact. I. Biphenyl, diphenylacetylene, and phenanthrene,
J. Phys. Chem., 1965, 69, 2935. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy S°gas Entropy of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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