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Diphenylacetylene

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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
Deltafgas385. ± 2.7kJ/molChydDavis, Allinger, et al., 1985ALS
Quantity Value Units Method Reference Comment
gas452.J/mol*KN/AAlcolea Palafox M., 1996This 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
Deltacsolid-7250. ± 1.kJ/molCcbCoops, Hoijtink, et al., 1953Corresponding «DELTA»fsolid = 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
297.5340.Kurbatov, 1950T = 65 to 303°C. Mp 61°C.; DH
225.9298.5Smith and Andrews, 1931T = 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
Tboil573.KN/AFarchan Laboratories, 1990BS
Quantity Value Units Method Reference Comment
Tfus333. ± 3.KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Deltasub95.3kJ/molCGC-DSCChickos, Hesse, et al., 1998AC
Deltasub95.1 ± 1.1kJ/molMEDiogo, Minas da Piedade, et al., 1993Based on data from 298. - 316. K.; AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
443.0.025Farchan Laboratories, 1990BS
443.20.025Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
63.8 ± 0.2440.EBSteele, Chirico, et al., 2002Based on data from 439. - 517. K.; AC
60.9 ± 0.2480.EBSteele, Chirico, et al., 2002Based on data from 439. - 517. K.; AC
58.1 ± 0.3520.EBSteele, Chirico, et al., 2002Based on data from 439. - 517. K.; AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
90.0 ± 4.5310.HSAChickos, Annunziata, et al., 1986Based on data from 299. - 321. K.; AC
88.7 ± 1.3313.N/AWolf and Weghofer, 1938Based on data from 299. - 321. K. See also Weghofer, 1938 and Jones, 1960.; AC
89. ± 1.317.VWolf and Weghofer, 1938, 2ALS

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
21.5335.DSCSteele, Chirico, et al., 2002AC
20.5334.N/ADomalski and Hearing, 1996AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

2-Cyclopropen-1-one, 2,3-diphenyl- = Diphenylacetylene + Carbon monoxide

By formula: C15H10O = C14H10 + CO

Quantity Value Units Method Reference Comment
Deltar-28. ± 5.0kJ/molCphaHung and Grabowski, 1992liquid phase; solvent: Alkane
Deltar18. ± 10.kJ/molCphaHerman and Goodman, 1989solid phase; solvent: Acetonitrile/water
Deltar-41. ± 12.kJ/molCphaGrabowski, Simon, et al., 1984liquid phase; solvent: Benzene

2Hydrogen + Diphenylacetylene = Bibenzyl

By formula: 2H2 + C14H10 = C14H14

Quantity Value Units Method Reference Comment
Deltar-249.5 ± 2.3kJ/molChydDavis, Allinger, et al., 1985liquid phase; solvent: Hexane
Deltar-268.6 ± 4.6kJ/molChydFlitcroft and Skinner, 1958solid 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 ± 0.03eVN/AN/AL

Electron affinity determinations

EA (eV) Method Reference Comment
<0.321 ± 0.074ECDWojnarovits and Foldiak, 1981G3MP2B3 calculations indicate an EA of ca. 0.2 eV; B

Ionization energy determinations

IE (eV) Method Reference Comment
7.95 ± 0.08PEElbel, Lienert, et al., 1981LLK
7.90 ± 0.02PEMaier and Turner, 1973LLK
8.0 ± 0.05PEEland, 1972LLK
7.91PERowland, 1971Unpublished result of J.H.D. Eland; LLK
23.4 ± 0.1EINatalis and Franklin, 1965RDSH
8.85 ± 0.05EINatalis and Franklin, 1965RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+20.7 ± 0.1?EINatalis and Franklin, 1965RDSH
C8H6+17.8 ± 0.1?EINatalis and Franklin, 1965RDSH
C9H5+21.3 ± 0.2?EINatalis and Franklin, 1965RDSH
C9H7+17.5 ± 0.1?EINatalis and Franklin, 1965RDSH
C10H6+18.2 ± 0.12C2H2EINatalis and Franklin, 1965RDSH
C11H7+17.5 ± 0.1?EINatalis and Franklin, 1965RDSH
C12H7+17.46 ± 0.06?EINatalis and Franklin, 1965RDSH
C12H8+15.58 ± 0.05?EINatalis and Franklin, 1965RDSH
C12H82+20.5 ± 0.1?EINatalis and Franklin, 1965RDSH
C14H8+16.66 ± 0.05H2EINatalis and Franklin, 1965RDSH
C14H9+15.1 ± 0.1HEINatalis and Franklin, 1965RDSH

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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

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Mass spectrum
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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

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), 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis 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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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]

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 «gamma»-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]


Notes

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, References