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Article: Through-space interactions between face-to-face, center-to-edge oriented arenes: Importance of polar-π effects

TitleThrough-space interactions between face-to-face, center-to-edge oriented arenes: Importance of polar-π effects
Authors
Issue Date2003
Citation
Organic and Biomolecular Chemistry, 2003, v. 1, n. 1, p. 157-162 How to Cite?
AbstractTwo series of conformationally restricted polycyclic compounds (1-3 and 4-7) have been synthesized as model systems for studying the through-space interactions between face-to-face, center-to-edge (parallel-offset) oriented arenes. These compounds feature different X substituents on one of the interacting rings. By monitoring the variation of the ΔG≠ for the rotation around the aryl-aryl bond in 1-7 as a function of X by 2D [1H, 1H] EXSY NMR spectroscopy, it was found that the barriers increase on passing from electron-donating to electron-withdrawing substituted derivatives. Quantum mechanical calculations [MP2/DVZ (2d,p)//B3LYP/DVZ(2nd.p)] gave barrier values and variations in agreement with the experimental data. The results are consistent with a repulsive arene-arene interaction dominated by electrostatic effects.
Persistent Identifierhttp://hdl.handle.net/10722/341060
ISSN
2023 Impact Factor: 2.9
2023 SCImago Journal Rankings: 0.607
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorCozzi, Franco-
dc.contributor.authorAnnunziata, Rita-
dc.contributor.authorBenaglia, Maurizio-
dc.contributor.authorCinquini, Mauro-
dc.contributor.authorRaimondi, Laura-
dc.contributor.authorBaldridge, Kim K.-
dc.contributor.authorSiegel, Jay S.-
dc.date.accessioned2024-03-13T08:39:50Z-
dc.date.available2024-03-13T08:39:50Z-
dc.date.issued2003-
dc.identifier.citationOrganic and Biomolecular Chemistry, 2003, v. 1, n. 1, p. 157-162-
dc.identifier.issn1477-0520-
dc.identifier.urihttp://hdl.handle.net/10722/341060-
dc.description.abstractTwo series of conformationally restricted polycyclic compounds (1-3 and 4-7) have been synthesized as model systems for studying the through-space interactions between face-to-face, center-to-edge (parallel-offset) oriented arenes. These compounds feature different X substituents on one of the interacting rings. By monitoring the variation of the ΔG≠ for the rotation around the aryl-aryl bond in 1-7 as a function of X by 2D [1H, 1H] EXSY NMR spectroscopy, it was found that the barriers increase on passing from electron-donating to electron-withdrawing substituted derivatives. Quantum mechanical calculations [MP2/DVZ (2d,p)//B3LYP/DVZ(2nd.p)] gave barrier values and variations in agreement with the experimental data. The results are consistent with a repulsive arene-arene interaction dominated by electrostatic effects.-
dc.languageeng-
dc.relation.ispartofOrganic and Biomolecular Chemistry-
dc.titleThrough-space interactions between face-to-face, center-to-edge oriented arenes: Importance of polar-π effects-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1039/b208871a-
dc.identifier.scopuseid_2-s2.0-0042035613-
dc.identifier.volume1-
dc.identifier.issue1-
dc.identifier.spage157-
dc.identifier.epage162-
dc.identifier.isiWOS:000181528500029-

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