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Anthracene

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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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - 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

C14H11+ + Anthracene = (C14H11+ bullet Anthracene)

By formula: C14H11+ + C14H10 = (C14H11+ bullet C14H10)

Quantity Value Units Method Reference Comment
Deltar16.0kcal/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar28.cal/mol*KN/AMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
6.1352.PHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M

Anthracene photodimer = 2Anthracene

By formula: C28H20 = 2C14H10

Quantity Value Units Method Reference Comment
Deltar-16.0kcal/molCmBendig, Buchwitz, et al., 1981liquid phase; solvent: Cyclohexane; Dimerization, see Bendig and Kreysig, 1981; ALS
Deltar6.9 ± 1.5kcal/molCmDonati, Guarini, et al., 1981solid phase; ALS

C14H10+ + Anthracene = (C14H10+ bullet Anthracene)

By formula: C14H10+ + C14H10 = (C14H10+ bullet C14H10)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar16.4kcal/molPHPMSMeot-Ner (Mautner), 1980gas phase; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KPHPMSMeot-Ner (Mautner), 1980gas phase; M

Maleic anhydride + Anthracene = Anthracene-maleic anhydride Diels-Alder adduct

By formula: C4H2O3 + C14H10 = C18H12O3

Quantity Value Units Method Reference Comment
Deltar-22. ± 0.5kcal/molCmKiselev, Mavrin, et al., 1982liquid phase; solvent: Benzene; ALS
Deltar-22.4kcal/molEqkLenz, Hegedus, et al., 1982liquid phase; solvent: 1,2,4-C6H3Cl3; ALS

1,4-Dewar anthracene = Anthracene

By formula: C14H10 = C14H10

Quantity Value Units Method Reference Comment
Deltar-77.4 ± 0.2kcal/molEqkDreeskamp, Kapahnke, et al., 1988liquid phase; solvent: Heptane; Isomerization; ALS

Anthracene + 2,5-Furnadione, 3-(1-methylethyl)- = C21H18O3

By formula: C14H10 + C7H8O3 = C21H18O3

Quantity Value Units Method Reference Comment
Deltar-20.9kcal/molEqkLenz, Hegedus, et al., 1982liquid phase; solvent: 1,2,4-C6H3Cl3; ALS

9,10-Dihydro-9,10-ethanoanthracene-11,11,12,12-tetracarbonitrile = Anthracene + Tetracyanoethylene

By formula: C20H10N4 = C14H10 + C6N4

Quantity Value Units Method Reference Comment
Deltar9.69 ± 0.50kcal/molCmRogers, 1972solid phase; ALS

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M., Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization, J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012 . [all data]

Bendig, Buchwitz, et al., 1981
Bendig, J.; Buchwitz, W.; Fischer, J.; Kreysig, D., Deactivation behavior of arenes and heteroarenes. XXXII. Effect of endo- and exocyclic substitution on the reversible dimerization behavior of anthracenes, J. Prakt. Chem., 1981, 323, 485-498. [all data]

Bendig and Kreysig, 1981
Bendig, J.; Kreysig, D., Deactivation behavior of arenes and heteroarenes. XXXI. A model of the reversible photodimerization of anthracene and 9-methylanthracene, J. Prakt. Chem., 1981, 323, 471-484. [all data]

Donati, Guarini, et al., 1981
Donati, D.; Guarini, G.G.T.; Sarti-Fantoni, P., Evaluation of the enthalpic change during the monomerization reaction of crystalline anthracene photodimer (AD), Mol. Cryst. Liq. Cryst., 1981, 69, 241-243. [all data]

Kiselev, Mavrin, et al., 1982
Kiselev, V.D.; Mavrin, G.V.; Konovalov, A.I., Thermodynamic principles of the occurrence of a Diels-Alder reaction in the presence of a Lewis acid, Zh. Org. Khim., 1982, 18, 2505-2510. [all data]

Lenz, Hegedus, et al., 1982
Lenz, T.G.; Hegedus, L.S.; Vaughan, J.D., Liquid phase thermochemical energy conversion systems - an application of Diels-Alder chemistry, Int. J. Energy Res., 1982, 6, 357-365. [all data]

Dreeskamp, Kapahnke, et al., 1988
Dreeskamp, H.; Kapahnke, P.; Tochtermann, W., Photo valence isomerization of sterically strained aromatic hydrocarbons: 8,9-dicarbethoxy[6]paracyclophane, Radiat. Phys. Chem., 1988, 32, 537-539. [all data]

Rogers, 1972
Rogers, F.E., Thermochemistry of the Diels-Alder reactions. II. Heat of addition of several dienes to tetracyanoethylene, J. Phys. Chem., 1972, 76, 106-109. [all data]


Notes

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