9,10-Anthracenedione
- Formula: C14H8O2
- Molecular weight: 208.2121
- IUPAC Standard InChI: InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H
- 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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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:
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 | -18.1 ± 0.69 | kcal/mol | Ccb | Ribeiro Da Silva, Ribeiro Da Silva, et al., 1989 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 18.62 | 100. | Singh S.N., 1969 | Comparison with values estimated by difference method [ Dorofeeva O.V., 1997] supposes that selected value of S(298.15 K) can be underestimated by 20 J/mol*K. Uncertainty of Cp(298.15 K) is evaluated as 10 J/mol*K.; GT |
| 32.206 | 200. | ||
| 47.271 | 298.15 | ||
| 47.569 | 300. | ||
| 62.185 | 400. | ||
| 74.833 | 500. | ||
| 85.031 | 600. | ||
| 92.923 | 700. | ||
| 99.809 | 800. | ||
| 105.23 | 900. | ||
| 109.77 | 1000. | ||
| 113.52 | 1100. | ||
| 116.63 | 1200. | ||
| 119.38 | 1300. | ||
| 121.68 | 1400. | ||
| 123.37 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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:
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 | -45.05 ± 0.67 | kcal/mol | Ccb | Ribeiro Da Silva, Ribeiro Da Silva, et al., 1989 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1544.9 ± 0.50 | kcal/mol | Ccb | Ribeiro Da Silva, Ribeiro Da Silva, et al., 1989 | Corresponding ΔfHºsolid = -45.05 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -1540.278 | kcal/mol | Ccb | Magnus, 1956 | Corresponding ΔfHºsolid = -49.698 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -1546.1 | kcal/mol | Ccb | Burriel, 1931 | Corresponding ΔfHºsolid = -43.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -1544.5 | kcal/mol | Ccb | Swietoslawski and Starczedska, 1925 | Corresponding ΔfHºsolid = -45.5 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 57.41 | 298.15 | Hildebrand, Duschak, et al., 1917 | T = 293 to 593 K. From heat content data.; DH |
Gas phase ion energetics 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 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, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
Ribeiro Da Silva, Ribeiro Da Silva, et al., 1989
Ribeiro Da Silva, M.A.V.; Ribeiro Da Silva, D.M.C.; Teixeira, J.A.S.,
Enthalpies of combustion of 1,4-naphthoquinone, 9,10-anthraquinone, 9,10-phenanthraquinone, 1,4,9,10-anthradiquinone, 5,8-dihydroxy-1,4-naphthoquinone, and 1,4-dihydroxy-9,10-anthraquinone,
J. Chem. Thermodyn., 1989, 21, 265-274. [all data]
Singh S.N., 1969
Singh S.N.,
Thermodynamic properties of some condensed ring quinones,
Indian J. Pure Appl. Phys., 1969, 7, 52-53. [all data]
Dorofeeva O.V., 1997
Dorofeeva O.V.,
Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]
Magnus, 1956
Magnus, A.,
Die resonanzenergien der parachinone Aui grund der prazisionsmessungsen ihrer verbrennungswarmen durch herrn gerhard wittwer,
Z. Phys. Chem. (Neue Folge), 1956, 9, 141-161. [all data]
Burriel, 1931
Burriel, F.,
7. Estudio fisico-quimico de algunos compuestos organicos solidos a la temperatura ordinaria, que se proponen como patrones de temperatura,
An. R. Soc. Esp. Fis. Quim., 1931, 29, 89-125. [all data]
Swietoslawski and Starczedska, 1925
Swietoslawski, W.; Starczedska, H.,
Correction des donnees thermochimiques de M.A. Valeur,
J. Chem. Phys., 1925, 22, 399-401. [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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid EA Electron affinity IE (evaluated) Recommended ionization energy ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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