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Bicyclo[2.2.1]hepta-2-ene-5-yl-7-ylium Radical Cation: A Theoretical Validation of a Bishomoaromatic Radical Cation Intermediate
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Quantum Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Quantum Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Quantum Chemistry.
2003 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 5, no 8, 1329-1331 p.Article in journal (Refereed) Published
Abstract [en]

[structure: see text] A natural bond orbital analysis of the distonic bicyclo[2.2.1]hepta-2-ene-5-yl-7-ylium radical cation interprets its structure and radical character by a three-center two-electron bond between C2, C3, and C7 (a bishomoaromatic stabilization) and a singly occupied orbital on C5, n(5). Moreover, B3LYP/6-311+G(d,p) ESR parameters, which agree excellently with experiment, are interpreted in terms of spin polarization in the natural hybrids of sigma(C5-H5), and a dual hyperconjugative effect involving n(5), sigma(C1-H1a), sigma(C1-H1b), and antibonding counterparts.

Place, publisher, year, edition, pages
2003. Vol. 5, no 8, 1329-1331 p.
National Category
Organic Chemistry Theoretical Chemistry
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URN: urn:nbn:se:uu:diva-47148DOI: 10.1021/ol034272tPubMedID: 12688751OAI: oai:DiVA.org:uu-47148DiVA: diva2:75055
Available from: 2007-02-08 Created: 2007-02-08 Last updated: 2017-12-05Bibliographically approved

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Salhi-Benachenhou, NessimaLunell, Sten

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