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Ethanedione, diphenyl-

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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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
gas480.18J/mol*KN/ADworkin A., 1983The value of 428.1 J/mol*K was obtained for the third-law entropy value at 298.15 K if other enthalpy of sublimation of benzil was used. However, statistical values of S(298.15 K) calculated by author [ Dworkin A., 1983] for different molecular models (382.3 and 405.3 J/mol*K) are considerably less than the calorimetric values.

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
Deltafsolid-154.0kJ/molCcbParks and Mosher, 1962ALS
Deltafsolid-179.kJ/molCcbSpringall and White, 1954ALS
Deltafsolid138.kJ/molCcbLandrieu, 1906ALS
Quantity Value Units Method Reference Comment
Deltacsolid-6784. ± 3.kJ/molCcbParks and Mosher, 1962Corresponding «DELTA»fsolid = -153.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-6760. ± 3.kJ/molCcbSpringall and White, 1954Corresponding «DELTA»fsolid = -179. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-6784.8kJ/molCcbBarker, 1925Author was aware that data differs from previously reported values; Corresponding «DELTA»fsolid = -154. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-6828.7kJ/molCcbLandrieu, 1906Corresponding «DELTA»fsolid = -110. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar292.08J/mol*KN/ADworkin A., 1983DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
245.7298.15Dworkin A., 1983T = 15 to 300 K.; 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity Value Units Method Reference Comment
Tboil619. - 621.KN/ABuckingham and Donaghy, 1982BS
Quantity Value Units Method Reference Comment
Tfus368. ± 1.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple368.020KN/AAndon and Connett, 1980Uncertainty assigned by TRC = 0.01 K; TRC
Ttriple368.000KN/AAndon and Connett, 1980Uncertainty assigned by TRC = 0.002 K; TRC
Quantity Value Units Method Reference Comment
Deltasub87.4kJ/molVSpringall and White, 1954ALS

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
461.0.016Buckingham and Donaghy, 1982BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
69.2416.AStephenson and Malanowski, 1987Based on data from 401. - 620. K. See also Stull, 1947.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
401.6 - 620.4.797292780.085-39.436Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
98.4 ± 1.1368.5VAihara, 1959crystal phase; ALS
98.4 ± 1.1329.N/AAihara, 1959, 2Based on data from 319. - 340. K. See also Cox and Pilcher, 1970 and Stephenson and Malanowski, 1987.; AC
82.8 ± 0.8311.VWolf and Weghofer, 1938ALS

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
22.88368.1N/AFattahi, Kass, et al., 2005AC
23.8369.2DSCRai and Varma, 2001AC
23.56368.N/ADomalski and Hearing, 1996AC
22.690368.05N/ABooss and Hauschildt, 1972DH

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
61.65368.05Booss and Hauschildt, 1972DH

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
0.584.Domalski and Hearing, 1996CAL
64.02368.

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.044184.07crystaline, IIcrystaline, IDworkin A., 1983DH
23.556368.022crystaline, IliquidAndon and Connett, 1980, 2DH
0.044184.07crystaline, IIcrystaline, IDworkin and Fuchs, 1977DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.5284.07crystaline, IIcrystaline, IDworkin A., 1983DH
64.01368.022crystaline, IliquidAndon and Connett, 1980, 2DH
0.5284.07crystaline, IIcrystaline, IDworkin and Fuchs, 1977DH

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:


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 compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IE (eV) Method Reference Comment
8.68 ± 0.05PIPolevoi, Matyuk, et al., 1987LBLHLM
8.72EIElder, Beynon, et al., 1976LLK
8.86 ± 0.15EIScheppele, Mitchum, et al., 1973LLK
8.78 ± 0.05EINatalis and Franklin, 1965RDSH
8.9 ± 0.05PEMcAlduff and Bunbury, 1979Vertical value; LLK
9.1PEArnett, Newkome, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+15.1 ± 0.2?EINatalis and Franklin, 1965RDSH
C7H5O+9.43 ± 0.05C6H5COPIPolevoi, Matyuk, et al., 1987LBLHLM
C7H5O+9.64C6H5COEIElder, Beynon, et al., 1976LLK
C7H5O+9.70 ± 0.05?EINatalis 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 TEXAS A&M UNIVERSITY, COLLEGE STATION, TEXAS, USA
NIST MS number 9668

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

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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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UVVis spectrum
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Additional Data

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Source Bartecki, Szoke, et al., 1961
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. 8965
Instrument Beckman DU
Melting point 94.8
Boiling point 347

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

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
PackedOV-1011768.Zenkevich, Acevedo, et al., 1991Celite 545 (0.20-0.25 mm), 10. K/min; Column length: 1.2 m; Tstart: 100. C; Tend: 300. C

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.

Dworkin A., 1983
Dworkin A., Heat capacity, phase transition, and thermodynamic properties of benzil, J. Chem. Thermodyn., 1983, 15, 1029-1035. [all data]

Parks and Mosher, 1962
Parks, G.S.; Mosher, H.P., Heats of combustion and formation of seven organic compounds containing oxygen, J. Chem. Phys., 1962, 37, 919-920. [all data]

Springall and White, 1954
Springall, H.D.; White, T.R., Heats of combustion and molecular structure. Part II. The mean bond energy term for the carbonyl system in certain ketones, J. Chem. Soc., 1954, 2765-27. [all data]

Landrieu, 1906
Landrieu, M.Ph., Thermochimie des hydrazones et des osazones, des dicetones-«alpha» et des sucres reducteurs, Compt. Rend., 1906, 140, 580-582. [all data]

Barker, 1925
Barker, M.F., Calorific value and constitution, J. Phys. Chem., 1925, 29, 1345-1363. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Andon and Connett, 1980
Andon, R.J.L.; Connett, J.E., Calibrants for thermal analysis. measurement of their enthalpies of fusion by adiabatic calorimetry., Thermochim. Acta, 1980, 42, 241. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Aihara, 1959
Aihara, A., Estimation of the energy of hydrogen bonds formed in crystals. I. Sublimation pressures of some organic molecular crystals and the additivity of lattice energy, Bull. Chem. Soc. Jpn., 1959, 32, 1242. [all data]

Aihara, 1959, 2
Aihara, Ariyuki, Estimation of the Energy of Hydrogen Bonds Formed in Crystals. I. Sublimation Pressures of Some Organic Molecular Crystals and the Additivity of Lattice Energy, Bull. Chem. Soc. Jpn., 1959, 32, 11, 1242-1248, https://doi.org/10.1246/bcsj.32.1242 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Fattahi, Kass, et al., 2005
Fattahi, Alireza; Kass, Steven R.; Liebman, Joel F.; Matos, M. Agostinha R.; Miranda, Margarida S.; Morais, Victor M.F., The Enthalpies of Formation of o -, m -, and p -Benzoquinone: Gas-Phase Ion Energetics, Combustion Calorimetry, and Quantum Chemical Computations Combined, J. Am. Chem. Soc., 2005, 127, 16, 6116-6122, https://doi.org/10.1021/ja042612f . [all data]

Rai and Varma, 2001
Rai, R.N.; Varma, K.B.R., Thermal and dielectric studies on binary organic system: benzil--m-nitroaniline, Materials Letters, 2001, 48, 6, 356-361, https://doi.org/10.1016/S0167-577X(00)00327-X . [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]

Booss and Hauschildt, 1972
Booss, H.J.; Hauschildt, K.R., Die Schmelzenthalpie des Benzils und 4-Nitrophenols, Z. Anal. Chem., 1972, 261(1), 32. [all data]

Andon and Connett, 1980, 2
Andon, R.J.L.; Connett, J.E., Calibrants for thermal analysis. Measurement of their enthalpies of fusion by adiabatic calorimetry, Thermochim. Acta, 1980, 42, 241-247. [all data]

Dworkin and Fuchs, 1977
Dworkin, A.; Fuchs, A.H., Heat capacity of benzil near its phase transition, J. Chem. Phys., 1977, 67, 1789-1790. [all data]

Polevoi, Matyuk, et al., 1987
Polevoi, A.V.; Matyuk, V.M.; Grigor'eva, G.A.; Potapov, V.K., Formation of intermediate products during the resonance stepwise polarization of dibenzyl ketone and benzil molecules, Russ. J. Phys. Chem., 1987, 21, 12. [all data]

Elder, Beynon, et al., 1976
Elder, J.F.; Beynon, J.H.; Cooks, R.G., The benzoyl ion. Thermochemistry and kinetic energy release, Org. Mass Spectrom., 1976, 11, 415. [all data]

Scheppele, Mitchum, et al., 1973
Scheppele, S.E.; Mitchum, R.K.; Kinneberg, K.F.; Meisels, G.G.; Emmel, R.H., Internal energy distributions and the fragmentation of gaseous organic ions. Dissociation of ions produced by electron impact on 4-methylbenzil, J. Am. Chem. Soc., 1973, 95, 5105. [all data]

Natalis and Franklin, 1965
Natalis, P.; Franklin, J.L., Ionization and dissociation of diphenyl and condensed ring aromatics by electron impact. II. Diphenylcarbonyls and ethers, J. Phys. Chem., 1965, 69, 2943. [all data]

McAlduff and Bunbury, 1979
McAlduff, E.J.; Bunbury, D.L., Photoelectron spectra of some aromatic mono-and di-ketones, J. Electron Spectrosc. Relat. Phenom., 1979, 17, 81. [all data]

Arnett, Newkome, et al., 1974
Arnett, J.F.; Newkome, G.; Mattice, W.L.; McGlynn, S.P., Excited electronic states of the «alpha»-dicarbonyls, J. Am. Chem. Soc., 1974, 96, 4385. [all data]

Bartecki, Szoke, et al., 1961
Bartecki, A.; Szoke, J.; Varsanyi, G.; Vizesy, M., Absorption spectra in the ultraviolet and visible region. Volume 2, Academic Press Inc., New York, 1961, 256. [all data]

Zenkevich, Acevedo, et al., 1991
Zenkevich, I.G.; Acevedo, J.M.; Aguilera, I.R., Increments of Gas Chromatographic Retention Indices for Characterization of Organic Reactions, Vestn. St. Petersb. Univ. Ser. 4: Fiz. Khim, 1991, 2, 51-56. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References