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- Publisher Website: 10.1021/ja0019981
- Scopus: eid_2-s2.0-0035977623
- PMID: 11456563
- WOS: WOS:000166650900001
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Article: Structure/energy correlation of bowl depth and inversion barrier in corannulene derivatives: Combined experimental and quantum mechanical analysis
Title | Structure/energy correlation of bowl depth and inversion barrier in corannulene derivatives: Combined experimental and quantum mechanical analysis |
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Authors | |
Issue Date | 2001 |
Citation | Journal of the American Chemical Society, 2001, v. 123, n. 4, p. 517-525 How to Cite? |
Abstract | Synthesis of a series of corannulene derivatives with varying bowl depths has allowed for a study correlating the structure (bowl depth) and the energy of bowl inversion. Substituents placed in the peri positions are repulsive and flatten the bowl, thus causing a decrease in the bowl inversion barrier. Conversely, annelation across the peri positions causes a deepening of the bowl, thus an increase in the bowl inversion barrier. Barriers between 8.7 and 17.3 kcal/mol have been measured, and their structures have been calculated using a variety of ab initio methods. The energy profile of an individual corannulene derivative is assumed to fit a mixed quartic/quadratic function from which an empirical correlation of bowl depth and inversion barrier that follows a quartic function is derived. Structure/energy correlations of this type speak broadly of the nature of enzymatic and catalytic activation of substrates. |
Persistent Identifier | http://hdl.handle.net/10722/341053 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Seiders, T. J. | - |
dc.contributor.author | Baldridge, K. K. | - |
dc.contributor.author | Grube, G. H. | - |
dc.contributor.author | Siegel, J. S. | - |
dc.date.accessioned | 2024-03-13T08:39:47Z | - |
dc.date.available | 2024-03-13T08:39:47Z | - |
dc.date.issued | 2001 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2001, v. 123, n. 4, p. 517-525 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/341053 | - |
dc.description.abstract | Synthesis of a series of corannulene derivatives with varying bowl depths has allowed for a study correlating the structure (bowl depth) and the energy of bowl inversion. Substituents placed in the peri positions are repulsive and flatten the bowl, thus causing a decrease in the bowl inversion barrier. Conversely, annelation across the peri positions causes a deepening of the bowl, thus an increase in the bowl inversion barrier. Barriers between 8.7 and 17.3 kcal/mol have been measured, and their structures have been calculated using a variety of ab initio methods. The energy profile of an individual corannulene derivative is assumed to fit a mixed quartic/quadratic function from which an empirical correlation of bowl depth and inversion barrier that follows a quartic function is derived. Structure/energy correlations of this type speak broadly of the nature of enzymatic and catalytic activation of substrates. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Structure/energy correlation of bowl depth and inversion barrier in corannulene derivatives: Combined experimental and quantum mechanical analysis | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja0019981 | - |
dc.identifier.pmid | 11456563 | - |
dc.identifier.scopus | eid_2-s2.0-0035977623 | - |
dc.identifier.volume | 123 | - |
dc.identifier.issue | 4 | - |
dc.identifier.spage | 517 | - |
dc.identifier.epage | 525 | - |
dc.identifier.isi | WOS:000166650900001 | - |