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Article: Conformational behaviour of medium-sized rings. Part III. Heterocyclic analogues of 12,13-dihydro-11H-dibenzo[a, e]cyclononene, 6,11,12,13-tetrahydro-5H-dibenzo[a, e]cyclononene, and 5,6,7,12,13,14-hexahydrodibenzo[a, f]cyclodecene
Title | Conformational behaviour of medium-sized rings. Part III. Heterocyclic analogues of 12,13-dihydro-11H-dibenzo[a, e]cyclononene, 6,11,12,13-tetrahydro-5H-dibenzo[a, e]cyclononene, and 5,6,7,12,13,14-hexahydrodibenzo[a, f]cyclodecene |
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Authors | |
Issue Date | 1976 |
Citation | Journal of the Chemical Society, Perkin Transactions 1, 1976, n. 9, p. 926-937 How to Cite? |
Abstract | The temperature dependence of the 1H n.m.r. spectra of a number of heterocyclic analogues (3a–c) of 12,13-dihydro-11H-dibenzo[a, e]cyclononene has been interpreted in terms of the interconversion of chair- and boat-like conformations. Conformational analysis on these molecules has been carried out with the aid of strain energy calculations on the thia-analogue (3c); in this case a useful correlation between calculated and experimental activation parameters was found. Variable temperature 1H n.m.r. spectroscopy and strain energy calculations have demonstrated that the heterocyclic analogues (4a–f) and (5a–d) of 6,11,12,13-tetrahydro-5H-dibenzo[a, f]-cyclononene and 5,6,7,12,13,14-hexahydrodibenzo[a, f]cyclodecene, respectively, all adopt flexible chair-like conformations with C2 symmetry which undergo an inversion process involving torsion about single bonds. © Royal Society of Chemistry. |
Persistent Identifier | http://hdl.handle.net/10722/332788 |
ISSN | |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Ollis, W. David | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:14:17Z | - |
dc.date.available | 2023-10-06T05:14:17Z | - |
dc.date.issued | 1976 | - |
dc.identifier.citation | Journal of the Chemical Society, Perkin Transactions 1, 1976, n. 9, p. 926-937 | - |
dc.identifier.issn | 1470-4358 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332788 | - |
dc.description.abstract | The temperature dependence of the 1H n.m.r. spectra of a number of heterocyclic analogues (3a–c) of 12,13-dihydro-11H-dibenzo[a, e]cyclononene has been interpreted in terms of the interconversion of chair- and boat-like conformations. Conformational analysis on these molecules has been carried out with the aid of strain energy calculations on the thia-analogue (3c); in this case a useful correlation between calculated and experimental activation parameters was found. Variable temperature 1H n.m.r. spectroscopy and strain energy calculations have demonstrated that the heterocyclic analogues (4a–f) and (5a–d) of 6,11,12,13-tetrahydro-5H-dibenzo[a, f]-cyclononene and 5,6,7,12,13,14-hexahydrodibenzo[a, f]cyclodecene, respectively, all adopt flexible chair-like conformations with C<sup>2</sup> symmetry which undergo an inversion process involving torsion about single bonds. © Royal Society of Chemistry. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the Chemical Society, Perkin Transactions 1 | - |
dc.title | Conformational behaviour of medium-sized rings. Part III. Heterocyclic analogues of 12,13-dihydro-11H-dibenzo[a, e]cyclononene, 6,11,12,13-tetrahydro-5H-dibenzo[a, e]cyclononene, and 5,6,7,12,13,14-hexahydrodibenzo[a, f]cyclodecene | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1039/P19760000926 | - |
dc.identifier.scopus | eid_2-s2.0-37049095965 | - |
dc.identifier.issue | 9 | - |
dc.identifier.spage | 926 | - |
dc.identifier.epage | 937 | - |
dc.identifier.isi | WOS:A1976BS33800002 | - |