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- Publisher Website: 10.1021/ja003383+
- Scopus: eid_2-s2.0-0035961493
- PMID: 11456777
- WOS: WOS:000167162100026
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Article: Quantum mechanical designs toward planar delocalized cyclooctatetraene: A new target for synthesis
Title | Quantum mechanical designs toward planar delocalized cyclooctatetraene: A new target for synthesis |
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Authors | |
Issue Date | 2001 |
Citation | Journal of the American Chemical Society, 2001, v. 123, n. 8, p. 1755-1759 How to Cite? |
Abstract | Ab 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 Identifier | http://hdl.handle.net/10722/341466 |
ISSN | 2021 Impact Factor: 16.383 2020 SCImago Journal Rankings: 7.115 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Baldridge, K. K. | - |
dc.contributor.author | Siegel, J. S. | - |
dc.date.accessioned | 2024-03-13T08:43:01Z | - |
dc.date.available | 2024-03-13T08:43:01Z | - |
dc.date.issued | 2001 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2001, v. 123, n. 8, p. 1755-1759 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/341466 | - |
dc.description.abstract | Ab 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.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Quantum mechanical designs toward planar delocalized cyclooctatetraene: A new target for synthesis | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja003383+ | - |
dc.identifier.pmid | 11456777 | - |
dc.identifier.scopus | eid_2-s2.0-0035961493 | - |
dc.identifier.volume | 123 | - |
dc.identifier.issue | 8 | - |
dc.identifier.spage | 1755 | - |
dc.identifier.epage | 1759 | - |
dc.identifier.isi | WOS:000167162100026 | - |