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
Go To: Top, Phase change data, Gas phase ion energetics 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 | 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 |
Phase change data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics 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:
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 573. | K | N/A | Farchan Laboratories, 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 333. ± 3. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 95.3 | kJ/mol | CGC-DSC | Chickos, Hesse, et al., 1998 | AC |
ΔsubH° | 95.1 ± 1.1 | kJ/mol | ME | Diogo, Minas da Piedade, et al., 1993 | Based on data from 298. to 316. K.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
443. | 0.025 | Farchan Laboratories, 1990 | BS |
443.2 | 0.025 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
63.8 ± 0.2 | 440. | EB | Steele, Chirico, et al., 2002 | Based on data from 439. to 517. K.; AC |
60.9 ± 0.2 | 480. | EB | Steele, Chirico, et al., 2002 | Based on data from 439. to 517. K.; AC |
58.1 ± 0.3 | 520. | EB | Steele, Chirico, et al., 2002 | Based on data from 439. to 517. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
90.0 ± 4.5 | 310. | HSA | Chickos, Annunziata, et al., 1986 | Based on data from 299. to 321. K.; AC |
88.7 ± 1.3 | 313. | N/A | Wolf and Weghofer, 1938 | Based on data from 299. to 321. K. See also Weghofer, 1938 and Jones, 1960.; AC |
89. ± 1. | 317. | V | Wolf and Weghofer, 1938, 2 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
21.5 | 335. | DSC | Steele, Chirico, et al., 2002 | AC |
20.5 | 334. | N/A | Domalski and Hearing, 1996 | AC |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, References, Notes
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 |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics 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]
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]
Farchan Laboratories, 1990
Farchan Laboratories,
Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]
Chickos, Hesse, et al., 1998
Chickos, James; Hesse, Donald; Hosseini, Sarah; Nichols, Gary; Webb, Paul,
Sublimation enthalpies at 298.15K using correlation gas chromatography and differential scanning calorimetry measurements,
Thermochimica Acta, 1998, 313, 2, 101-110, https://doi.org/10.1016/S0040-6031(97)00432-2
. [all data]
Diogo, Minas da Piedade, et al., 1993
Diogo, Hermínio P.; Minas da Piedade, Manuel E.; Fernandes, Anabela C.; Martinho Simões, José A.; Ribeiro da Silva, Manuel A.V.; Monte, Manuel J.S.,
The enthalpy of sublimation of diphenylacetylene from Knudsen effusion studies,
Thermochimica Acta, 1993, 228, 15-22, https://doi.org/10.1016/0040-6031(93)80269-G
. [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]
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, Annunziata, et al., 1986
Chickos, J.S.; Annunziata, R.; Ladon, L.H.; Hyman, A.S.; Liebman, J.F.,
Estimating heats of sublimation of hydrocarbons. A semiempirical approach,
J. Org. Chem., 1986, 51, 4311-4314. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.Z.,
Z. Phys. Chem. Abt. B, 1938, 39, 194. [all data]
Weghofer, 1938
Weghofer, H.,
, Ph.D. Dissertation, Phys. Chem. Institut der Universital Halle, 1938. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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, Phase change data, Gas phase ion energetics data, 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 Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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