Ethanedione, diphenyl-
- Formula: C14H10O2
- Molecular weight: 210.2280
- IUPAC Standard InChIKey: WURBFLDFSFBTLW-UHFFFAOYSA-N
- CAS Registry Number: 134-81-6
- 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: Benzil; Bibenzoyl; Dibenzoyl; Diphenyl-α,β-diketone; Diphenylethanedione; Diphenylglyoxal; 1,2-Diphenylethane-1,2-dione; 1,2-Diphenylethanedione; Glyoxal, diphenyl-; Wy 20910; 1,2-Ethanedione, 1,2-diphenyl-; NSC 220315
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Gas phase thermochemistry data
Go To: Top, Condensed 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 compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
S°gas | 480.18 | J/mol*K | N/A | Dworkin A., 1983 | The 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
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 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 |
---|---|---|---|---|---|
ΔfH°solid | -154.0 | kJ/mol | Ccb | Parks and Mosher, 1962 | ALS |
ΔfH°solid | -179. | kJ/mol | Ccb | Springall and White, 1954 | ALS |
ΔfH°solid | 138. | kJ/mol | Ccb | Landrieu, 1906 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -6784. ± 3. | kJ/mol | Ccb | Parks and Mosher, 1962 | Corresponding ΔfHºsolid = -153.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -6760. ± 3. | kJ/mol | Ccb | Springall and White, 1954 | Corresponding ΔfHºsolid = -179. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -6784.8 | kJ/mol | Ccb | Barker, 1925 | Author was aware that data differs from previously reported values; Corresponding ΔfHºsolid = -154. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -6828.7 | kJ/mol | Ccb | Landrieu, 1906 | Corresponding ΔfHºsolid = -110. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 292.08 | J/mol*K | N/A | Dworkin A., 1983 | DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
245.7 | 298.15 | Dworkin A., 1983 | T = 15 to 300 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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
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 |
---|---|---|---|---|---|
Tboil | 619. to 621. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 368. ± 1. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 368.020 | K | N/A | Andon and Connett, 1980 | Uncertainty assigned by TRC = 0.01 K; TRC |
Ttriple | 368.000 | K | N/A | Andon and Connett, 1980 | Uncertainty assigned by TRC = 0.002 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 87.4 | kJ/mol | V | Springall and White, 1954 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
461. | 0.016 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
69.2 | 416. | A | Stephenson and Malanowski, 1987 | Based on data from 401. to 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 to 620. | 4.79729 | 2780.085 | -39.436 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
98.4 ± 1.1 | 368.5 | V | Aihara, 1959 | crystal phase; ALS |
98.4 ± 1.1 | 329. | N/A | Aihara, 1959, 2 | Based on data from 319. to 340. K. See also Cox and Pilcher, 1970 and Stephenson and Malanowski, 1987.; AC |
82.8 ± 0.8 | 311. | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
22.88 | 368.1 | N/A | Fattahi, Kass, et al., 2005 | AC |
23.8 | 369.2 | DSC | Rai and Varma, 2001 | AC |
23.56 | 368. | N/A | Domalski and Hearing, 1996 | AC |
22.690 | 368.05 | N/A | Booss and Hauschildt, 1972 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
61.65 | 368.05 | Booss and Hauschildt, 1972 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.5 | 84. | Domalski and Hearing, 1996 | CAL |
64.02 | 368. |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.0441 | 84.07 | crystaline, II | crystaline, I | Dworkin A., 1983 | DH |
23.556 | 368.022 | crystaline, I | liquid | Andon and Connett, 1980, 2 | DH |
0.0441 | 84.07 | crystaline, II | crystaline, I | Dworkin and Fuchs, 1977 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.52 | 84.07 | crystaline, II | crystaline, I | Dworkin A., 1983 | DH |
64.01 | 368.022 | crystaline, I | liquid | Andon and Connett, 1980, 2 | DH |
0.52 | 84.07 | crystaline, II | crystaline, I | Dworkin and Fuchs, 1977 | DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, 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-α 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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°gas Entropy of gas at standard conditions S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy 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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