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The structure, modelling and dynamics of 2, 7-diisopropoxy-1, 8-diarylnaphthalenes

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dc.contributor.author Nasser, Rima
dc.contributor.author Thirsk, Carl
dc.contributor.author Hawkes, Geoffrey E.
dc.contributor.author Kroemer, Romano T.
dc.contributor.author Liedl, Klaus R.
dc.contributor.author Loertinh, Thomas
dc.date.accessioned 2019-04-09T09:04:38Z
dc.date.available 2019-04-09T09:04:38Z
dc.date.copyright 2002 en_US
dc.identifier.issn 1364-5471 en_US
dc.identifier.uri http://hdl.handle.net/10725/10379
dc.description.abstract 2,7-Diisopropoxy-1,8-dibromonaphthalene 5 was prepared in two steps from 2,7-dihydroxynaphthalene and was coupled under Suzuki cross-coupling conditions with boronic acids 9 and 10 to provide the corresponding 1,8-diarylnaphthalene systems 12a and 13a respectively. In contrast, attempted coupling of dibromide 5 with o-tolylboronic acid 11 proved unrewarding. Single crystal X-ray structure determination of compounds 12a and 13a showed that both structures possessed a high degree of structural deformation due to high internal steric repulsions between the 1,8-diaryl rings and their substituents. Dynamic 1H NMR experiments showed that these two systems possessed very slow phenyl–naphthalene bond rotation (ca. 2 s−1), corresponding to rotation barriers (ΔG*) of 16–18 kcal mol−1. Molecular modelling predicts that such systems have approximately similar rotation barriers and that in order to completely prevent phenyl–naphthalene bond rotation, an ortho-phenyl substituent is required, with a barrier to rotation of ca. 40 kcal mol−1. en_US
dc.language.iso en en_US
dc.title The structure, modelling and dynamics of 2, 7-diisopropoxy-1, 8-diarylnaphthalenes en_US
dc.type Article en_US
dc.description.version Published en_US
dc.author.school SOM en_US
dc.author.idnumber 200904844 en_US
dc.author.department N/A en_US
dc.description.embargo N/A en_US
dc.relation.journal Journal of the Chemical Society, Perkin Transactions 2 en_US
dc.journal.issue 2 en_US
dc.article.pages 1510-1519 en_US
dc.identifier.ctation Thirsk, C., Hawkes, G. E., Kroemer, R. T., Liedl, K. R., Loerting, T., Nasser, R., ... & Whiting, A. (2002). The structure, modelling and dynamics of 2, 7-diisopropoxy-1, 8-diarylnaphthalenes. Journal of the Chemical Society, Perkin Transactions 2, (9), 1510-1519. en_US
dc.author.email rima.nasser@lau.edu.lb en_US
dc.identifier.tou http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php en_US
dc.identifier.url https://pubs.rsc.org/en/content/articlelanding/2002/p2/b201235a/unauth#!divAbstract en_US
dc.author.affiliation Lebanese American University en_US


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