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- Publisher Website: 10.1021/jo010571p
- Scopus: eid_2-s2.0-0035966233
- PMID: 11749597
- WOS: WOS:000172993000002
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Article: Persistent oxidation dications from twisted fluoranthenes, benzo[k]fluoranthene and dimethyldibenzo[j.l]fluoranthene: Charge delocalization mode, tropicity, and formation of novel 8,8′-bifluoranthenyls. An NMR and theoretical study
Title | Persistent oxidation dications from twisted fluoranthenes, benzo[k]fluoranthene and dimethyldibenzo[j.l]fluoranthene: Charge delocalization mode, tropicity, and formation of novel 8,8′-bifluoranthenyls. An NMR and theoretical study |
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Authors | |
Issue Date | 2001 |
Citation | Journal of Organic Chemistry, 2001, v. 66, n. 26, p. 8701-8708 How to Cite? |
Abstract | First examples of persistent oxidation dications from fluoranthene-PAHs namely 1,3,4,6,7,10-hexamethyl- 2 and 3,4-dichloro-1,6,7,10-tetramethylfluoranthene 3, benzo[k]fluoranthene 6, and 3,6-dimethyldibenzo[j,l]fluoranthene 9 are reported. Charge delocalization mode and tropicity in the resulting nonalternant dications are examined. Quenching of the superacid solutions of the dications resulted in the formation of novel 8,8′-bifluoranthenyls 2a-4a. AM1 was used as an initial guide for dication generation (ΔΔHf° and ionization potentials) and for probing the structures of the crowded fluoranthene substrates and their bifluoranthenyls. In selected cases, the dications and their neutral precursors were calculated at the B3LYP/6-31G(d,p) level. Charge delocalization mode (difference in NPA charges) and DFT/GIAO-derived NMR chemical shifts were obtained for comparison with experiment; aromaticity was assessed via nucleus independent chemical shift (NICS) calculations. |
Persistent Identifier | http://hdl.handle.net/10722/341007 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Laali, K. K. | - |
dc.contributor.author | Okazaki, T. | - |
dc.contributor.author | Galembeck, S. E. | - |
dc.contributor.author | Siegel, J. S. | - |
dc.date.accessioned | 2024-03-13T08:39:25Z | - |
dc.date.available | 2024-03-13T08:39:25Z | - |
dc.date.issued | 2001 | - |
dc.identifier.citation | Journal of Organic Chemistry, 2001, v. 66, n. 26, p. 8701-8708 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10722/341007 | - |
dc.description.abstract | First examples of persistent oxidation dications from fluoranthene-PAHs namely 1,3,4,6,7,10-hexamethyl- 2 and 3,4-dichloro-1,6,7,10-tetramethylfluoranthene 3, benzo[k]fluoranthene 6, and 3,6-dimethyldibenzo[j,l]fluoranthene 9 are reported. Charge delocalization mode and tropicity in the resulting nonalternant dications are examined. Quenching of the superacid solutions of the dications resulted in the formation of novel 8,8′-bifluoranthenyls 2a-4a. AM1 was used as an initial guide for dication generation (ΔΔHf° and ionization potentials) and for probing the structures of the crowded fluoranthene substrates and their bifluoranthenyls. In selected cases, the dications and their neutral precursors were calculated at the B3LYP/6-31G(d,p) level. Charge delocalization mode (difference in NPA charges) and DFT/GIAO-derived NMR chemical shifts were obtained for comparison with experiment; aromaticity was assessed via nucleus independent chemical shift (NICS) calculations. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of Organic Chemistry | - |
dc.title | Persistent oxidation dications from twisted fluoranthenes, benzo[k]fluoranthene and dimethyldibenzo[j.l]fluoranthene: Charge delocalization mode, tropicity, and formation of novel 8,8′-bifluoranthenyls. An NMR and theoretical study | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/jo010571p | - |
dc.identifier.pmid | 11749597 | - |
dc.identifier.scopus | eid_2-s2.0-0035966233 | - |
dc.identifier.volume | 66 | - |
dc.identifier.issue | 26 | - |
dc.identifier.spage | 8701 | - |
dc.identifier.epage | 8708 | - |
dc.identifier.isi | WOS:000172993000002 | - |