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 |
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:
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 |
---|---|---|---|---|---|
ΔcH°solid | -7250. ± 1. | kJ/mol | Ccb | Coops, Hoijtink, et al., 1953 | Corresponding ΔfHºsolid = 312. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
297.5 | 340. | Kurbatov, 1950 | T = 65 to 303°C. Mp 61°C.; DH |
225.9 | 298.5 | Smith and Andrews, 1931 | T = 102 to 323 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
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 |
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 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- SOLID (SPLIT MULL), FLUOROLUBE FOR 3800-1330 CM-1, NUJOL FOR 1330-400 CM-1; BECKMAN IR-9 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (10% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-400 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
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
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-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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Download spectrum in JCAMP-DX format.
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 |
Gas Chromatography
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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
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 283.2 | Wang, Hou, et al., 2007 | 30. m/0.30 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
Capillary | HP-5 | 289.27 | Piao, Chu, et al., 1999 | 30. m/0.25 mm/0.25 μm, 50. C @ 2. min, 4. K/min, 280. C @ 20. min |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5MS | 291.7 | Aracil, Font, et al., 2005 | Column length: 60. m; Column diameter: 0.25 mm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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]
Coops, Hoijtink, et al., 1953
Coops, J.; Hoijtink, G.J.; Kramer, Th.J.E.; Faber, A.C.,
Thermochemical investigations on arylethynes I. Heats of combustion of some diarylethynes,
Rec. Trav. Chim. Pays/Bas, 1953, 72, 781. [all data]
Kurbatov, 1950
Kurbatov, V.Ya.,
Specific heats of liquids. III. Specific heat of hydrocarbons with several noncondensed rings,
Zhur. Obshch. Khim., 1950, 20, 1139-1144. [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]
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]
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]
Wang, Hou, et al., 2007
Wang, G.; Hou, Z.; Sun, Y.; Liu, Y.; Xie, B.; Liu, S.,
Investigation of pyrolysis behavior of fenoxycarb using PY-GC-MS assisted with chemometric methods,
Chem. Anal., 2007, 52, 141-156. [all data]
Piao, Chu, et al., 1999
Piao, M.; Chu, S.; Zheng, M.; Xu, X.,
Characterization of the combustion products of polyethylene,
Chemosphere, 1999, 39, 9, 1497-1512, https://doi.org/10.1016/S0045-6535(99)00054-5
. [all data]
Aracil, Font, et al., 2005
Aracil, I.; Font, R.; Conesa, J.A.,
Semivolatile and volatile compounds from the pyrolysis and combustion of polyvinyl chloride,
J. Anal. Appl. Pyrolysis, 2005, 74, 1-2, 465-478, https://doi.org/10.1016/j.jaap.2004.09.008
. [all data]
Notes
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- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid EA Electron affinity IE (evaluated) Recommended ionization energy S°gas Entropy of gas at standard conditions Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions 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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