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Article: Quantum mechanical designs toward planar delocalized cyclooctatetraene: A new target for synthesis

TitleQuantum mechanical designs toward planar delocalized cyclooctatetraene: A new target for synthesis
Authors
Issue Date2001
Citation
Journal of the American Chemical Society, 2001, v. 123, n. 8, p. 1755-1759 How to Cite?
AbstractAb initio and hybrid density functional quantum mechanical computation are applied to the structure and energetics of a series of annelated cyclooctatetraenes. Tetrakis-cyclobuteno, perfluorocyclobuteno or bicyclo-[2.1.1]hexeno annelations result in planar structures with distinct exo and endo valence tautomers of the double bonded cycle. The contribution of each basic annelation to the exo/endo relative energy is estimated. An additivity scheme for approximating the energy of a mixed system is developed and compared to the quantum mechanical prediction. Bis bicyclic annelation to the a and d positions creates "valence tautomeric frustration" and strongly perturbs the molecular structure. This phenomenon leads to a general design for a planar cyclooctatetraenes where the "delocalized" diradicaloid state is the minimum energy form. These compounds are seen as excellent targets for chemical synthesis.
Persistent Identifierhttp://hdl.handle.net/10722/341466
ISSN
2021 Impact Factor: 16.383
2020 SCImago Journal Rankings: 7.115
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorBaldridge, K. K.-
dc.contributor.authorSiegel, J. S.-
dc.date.accessioned2024-03-13T08:43:01Z-
dc.date.available2024-03-13T08:43:01Z-
dc.date.issued2001-
dc.identifier.citationJournal of the American Chemical Society, 2001, v. 123, n. 8, p. 1755-1759-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/341466-
dc.description.abstractAb initio and hybrid density functional quantum mechanical computation are applied to the structure and energetics of a series of annelated cyclooctatetraenes. Tetrakis-cyclobuteno, perfluorocyclobuteno or bicyclo-[2.1.1]hexeno annelations result in planar structures with distinct exo and endo valence tautomers of the double bonded cycle. The contribution of each basic annelation to the exo/endo relative energy is estimated. An additivity scheme for approximating the energy of a mixed system is developed and compared to the quantum mechanical prediction. Bis bicyclic annelation to the a and d positions creates "valence tautomeric frustration" and strongly perturbs the molecular structure. This phenomenon leads to a general design for a planar cyclooctatetraenes where the "delocalized" diradicaloid state is the minimum energy form. These compounds are seen as excellent targets for chemical synthesis.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleQuantum mechanical designs toward planar delocalized cyclooctatetraene: A new target for synthesis-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja003383+-
dc.identifier.pmid11456777-
dc.identifier.scopuseid_2-s2.0-0035961493-
dc.identifier.volume123-
dc.identifier.issue8-
dc.identifier.spage1755-
dc.identifier.epage1759-
dc.identifier.isiWOS:000167162100026-

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