Aromatic polycyclic benzenoid tetraanions: pyrene and perylene anions revisited

Minsky, Abraham; Klein, Joseph; Rabinovitz, Mordecai

doi:10.1021/ja00405a053

Cited by 16 publications

(2 citation statements)

References 4 publications

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“…Diese Argumentation leitet sich aus den Erfahrungen mit den Radikalanionen von Cyclophanen ab [24] [25] [26]. berechneten Spinpopulation (e,: NLUMO) an C(1) and C (6). Die .…”

Section: Discussionunclassified

Radikaltrianionen von Isopyrenen

Huber¹

1983

Helvetica Chimica Acta

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Radical Trianions of Isopyrenes SummaryThe radical trianions derived from acepleiadylene (l), dicyclopenta[eA kllheptalene (2) and dicyclohepta[cd, gh]-pentalene (3) are described. Whereas the hyperfine data of 13; and Z3; are consistent with the predictions of an HMO-McLachlan-procedure, the corresponding data of 33; substantially differ from the calculated values. The spin distribution in 337 is polarized by the counterions in such a way, that the hyperfine data of this radical trianion no longer reflect theDZh-symmetry of the neutral compound3 and the radical anion 3;. In addition, the interaction of the charged organic ion 33: with the counterions influences the energy of the low-lying antibonding molecular orbitals LUMO (lowest unoccupied molecular orbital) and NLUMO (next lowest unoccupied molecular orbital). The passage from a looser ion pair (33:/3Li+) to a tighter ion pair (33T/3Na', 33T/3Kt) causes a change in the orbital sequence of LUMO and NLUMO.

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“…Diese Argumentation leitet sich aus den Erfahrungen mit den Radikalanionen von Cyclophanen ab [24] [25] [26]. berechneten Spinpopulation (e,: NLUMO) an C(1) and C (6). Die .…”

Section: Discussionunclassified

Radikaltrianionen von Isopyrenen

Huber¹

1983

Helvetica Chimica Acta

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“…[36] Semiempirical calculations predict that the torsion Phenanthrene 14π 7.68 [44] angle decreases from 95.1% in the neutral species to 83.0% Phenanthrene dianion 16π 1.34 [44] 6 14π (ϫ 2) 7.93 in the dianion in contrast to 61.0% in the charged tetra- despite the coulombic repulsions described above. In fact, Pyrene dianion 16π 0.97 [45,46] localization of larger charge densities at C3 and C9 along 7 14π (ϫ 2) 8.12…”

Section: Isotope Shift Effectsmentioning

confidence: 99%

π-Conjugated Benzoperylenes: Sequential C–S Bond Cleavage and Charge Distribution Patterns of the Anions

Benshafrut

Rabinovitz²,

Hoffman

et al. 1999

Eur. J. Org. Chem.

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Chemical reduction of polyaromatic hydrocarbons yielded solutions of long‐lived polyanionic species. Reduction of a sulfur heterocycle afforded a stable sulfur‐containing dianion. Sulfur extrusion from this dianion proceeded upon further contact with the reducing metal. NMR and UV studies indicate a sulfur extrusion mechanism different than that previously observed in THF. Electron transfer to the already reduced hydrocarbon skeleton results in the stepwise cleavage of the two C–S bonds and the extrusion of a sulfur atom. Dimers of aromatic hydrocarbons such as pyrene and phenanthrene have been reduced as well. The interplay between coulombic repulsions and resonance energies is described.

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With Adducts of Conjugated Hydrocarbons in Donor Solvents

Grovenstein¹

1988

Inorganic Reactions and Methods

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Aromatic polycyclic benzenoid tetraanions: pyrene and perylene anions revisited

Cited by 16 publications

References 4 publications

Radikaltrianionen von Isopyrenen

Radikaltrianionen von Isopyrenen

π-Conjugated Benzoperylenes: Sequential C–S Bond Cleavage and Charge Distribution Patterns of the Anions

With Adducts of Conjugated Hydrocarbons in Donor Solvents

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