9,10-Anthracenedione
- Formula: C14H8O2
- Molecular weight: 208.2121
- IUPAC Standard InChIKey: RZVHIXYEVGDQDX-UHFFFAOYSA-N
- CAS Registry Number: 84-65-1
- 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: Anthraquinone; Anthradione; Hoelite; Morkit; 9,10-Anthraquinone; Anthracene, 9,10-dihydro-9,10-dioxo-; 9,10-Dioxoanthracene; 9,10-Anthrachinon; Corbit; Anthracene-9,10-quinone; NSC 7957; anthracene-9,10-dione; 9,10-anthracenequinone
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Phase change data
Go To: Top, 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
DRB - Donald R. Burgess, Jr.
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 |
---|---|---|---|---|---|
Tboil | 653.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 650. | K | N/A | Burriel, 1931 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 558. ± 2. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 114. ± 20. | kJ/mol | AVG | N/A | Average of 8 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
64.3 | 574. | A | Stephenson and Malanowski, 1987 | Based on data from 559. to 660. K.; 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 |
---|---|---|---|---|---|
463. to 653.1 | 2.69646 | 970.529 | -291.767 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
98.3 | 413. | GS | NISHIDA, ISHIHARA, et al., 2008 | Based on data from 373. to 453. K. See also Nishida, Ishihara, et al., 1978.; AC |
107.5 ± 0.8 | 434. | ME | Bardi, Gigli, et al., 1973 | AC |
107.9 ± 0.8 | 397. to 471. | ME | Bardi, Gigli, et al., 1973 | AC |
127.0 ± 3.0 | 470. to 590. | C | Beech and Lintonbon, 1971 | AC |
126.4 | 373. | ME | Hoyer and Peperle, 1958 | Based on data from 343. to 403. K. See also Stephenson and Malanowski, 1987.; AC |
104.6 | 367. | ME | Inokuchi, Shiba, et al., 1952 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
32.57 | 558. | Domalski and Hearing, 1996 | AC |
32.570 | 555. | Hildebrand, Duschak, et al., 1917 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
58.7 | 555. | Hildebrand, Duschak, et al., 1917 | DH |
Gas phase ion energetics data
Go To: Top, 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:
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
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.25 ± 0.12 | eV | N/A | N/A | L |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.591 ± 0.061 | TDEq | Heinis, Chowdhury, et al., 1988 | ΔGea(423 K) = -35.4 kcal/mol; ΔSea = -2.9 eu.; B |
1.15 ± 0.10 | SI | Page and Goode, 1969 | The Magnetron method, lacking mass analysis, is not considered reliable.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.0 | PE | Gleiter, Dobler, et al., 1987 | LBLHLM |
9.25 | PE | Lauer, Schafer, et al., 1975 | LLK |
9.40 ± 0.08 | EI | Zaretskii, Sadovskaya, et al., 1971 | LLK |
9.25 ± 0.03 | PI | Potapov and Sorokin, 1971 | LLK |
9.3 | PI | Terenin, 1961 | RDSH |
References
Go To: Top, 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.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Burriel, 1931
Burriel, F.,
Physico-Chemical Study of Some Solid Organic Compounds at Ordinary Temperatures, and Their COrrelationo with Temperature,
An. R. Soc. Esp. Fis. Quim., 1931, 29, 89. [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]
NISHIDA, ISHIHARA, et al., 2008
NISHIDA, K.; ISHIHARA, E.; OSAKA, T.; KOUKITU, M.,
Vapour Pressures and Heats of Sublimation of Some Disperse Dyes,
J Food Science, 2008, 93, 2, 52-54, https://doi.org/10.1111/j.1478-4408.1977.tb03324.x
. [all data]
Nishida, Ishihara, et al., 1978
Nishida, K.; Ishihara, E.; Osaka, T.; Koukitu, M.,
Vapor pressures and heats of sublimation of some disperse dyes,
Galaxia, 1978, 72, 13. [all data]
Bardi, Gigli, et al., 1973
Bardi, Giampiero; Gigli, Rosario; Malaspina, Leopoldo; Piacente, Vincenzo,
Vapor pressure and sublimation enthalpy of anthraquinone and of 1,5- and 1,8-dihydroxyanthraquinones,
J. Chem. Eng. Data, 1973, 18, 2, 126-130, https://doi.org/10.1021/je60057a024
. [all data]
Beech and Lintonbon, 1971
Beech, Graham; Lintonbon, Roger M.,
The measurement of sublimation enthalpies by differential scanning calorimetry,
Thermochimica Acta, 1971, 2, 1, 86-88, https://doi.org/10.1016/0040-6031(71)85027-X
. [all data]
Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W.,
Z. Elektrochem., 1958, 62, 61. [all data]
Inokuchi, Shiba, et al., 1952
Inokuchi, Hiroo; Shiba, Sukekuni; Handa, Takashi; Akamatu, Hideo,
Heats of Sublimation of Condensed Polynuclear Aromatic Hydrocarbons,
Bull. Chem. Soc. Jpn., 1952, 25, 5, 299-302, https://doi.org/10.1246/bcsj.25.299
. [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]
Hildebrand, Duschak, et al., 1917
Hildebrand, J.H.; Duschak, A.D.; Foster, A.H.,
and Beebe, C.W. The specific heats and heats of fusion of triphenylmethane, anthraquinone and anthracene,
J. Am. Chem. Soc., 1917, 39, 2293-2297. [all data]
Heinis, Chowdhury, et al., 1988
Heinis, T.; Chowdhury, S.; Scott, S.L.; Kebarle, P.,
Electron Affinities of Benzo-, Naphtho-, and Anthraquinones Determined from Gas-Phase Equilibria Measurements,
J. Am. Chem. Soc., 1988, 110, 2, 400, https://doi.org/10.1021/ja00210a015
. [all data]
Page and Goode, 1969
Page, F.M.; Goode, G.C.,
Negative Ions and the Magnetron., Wiley, NY, 1969. [all data]
Gleiter, Dobler, et al., 1987
Gleiter, R.; Dobler, W.; Vogel, E.; Bohm, S.; Lex, J.,
Consequences of n/o interactions in bishomoanthraquinones and their dimethylene derivatives. A structural and PE spectroscopic study,
J. Am. Chem. Soc., 1987, 109, 5156. [all data]
Lauer, Schafer, et al., 1975
Lauer, G.; Schafer, W.; Schweig, A.,
Assignment of the four lowest ionized states of p-benzoquinone and the question of "lone pair" splitting in this system,
Chem. Phys. Lett., 1975, 33, 312. [all data]
Zaretskii, Sadovskaya, et al., 1971
Zaretskii, V.I.; Sadovskaya, V.L.; Wulfson, N.S.; Sizoy, V.F.; Merimson, V.G.,
Mass spectrometry of steroid systems-XXI. Appearance and ionization potentials for the stereoisomers of the D-homoestrane series,
Org. Mass Spectrom., 1971, 5, 1179. [all data]
Potapov and Sorokin, 1971
Potapov, V.K.; Sorokin, V.V.,
Photoionization and ion-molecule reactions in quinones and alcohols,
High Energy Chem., 1971, 5, 435, In original 487. [all data]
Terenin, 1961
Terenin, A.,
Charge transfer in organic solids, induced by light,
Proc. Chem. Soc., London, 1961, 321. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point 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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