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Article: Conformational behaviour of medium-sized rings. Part 9. disalicylides and trisalicylides
Title | Conformational behaviour of medium-sized rings. Part 9. disalicylides and trisalicylides |
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Authors | |
Issue Date | 1982 |
Citation | Journal of the Chemical Society, Perkin Transactions 1, 1982, p. 1629-1636 How to Cite? |
Abstract | The temperature dependences of the 1H n.m.r. spectra of di-o-thymotide (13) and di-o-carvacrotide (14) have been interpreted in terms of ring inversion (12a) ⇌ (12b) between enantiomeric boat conformations. Comparison of the ΔG‡values (17.7 and 18.4 kcal mol−1, respectively) for this conformational change suggests that it takes place by a pseudorotational process involving folded boat conformations (17) in which the substituents (methyl and isopropyl, respectively) on C-3 enter into 1,5-interactions with the carbonyl oxygen atoms in the eight-membered rings at the rate-determining transition states. The temperature dependences of the 1H n.m.r. spectra of tri-o-cresotide (6) and tri-m-cresotide (7) provide further evidence that a mechanism involving pedalling of trans-ester linkages through the mean plane of the twelve-membered ring accounts for the conformational changes between enantiomeric propeller (4) and helical (5) conformations. The ΔG‡values for interconversion and inversion processes of eight- and twelve-membered ring compounds show an informative dependence upon the steric demands of the ortho-substituents on the aromatic rings. © Royal Society of Chemistry. |
Persistent Identifier | http://hdl.handle.net/10722/332793 |
ISSN | |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Ollis, W. David | - |
dc.contributor.author | Stephanatou, Julia Stephanidou | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:14:19Z | - |
dc.date.available | 2023-10-06T05:14:19Z | - |
dc.date.issued | 1982 | - |
dc.identifier.citation | Journal of the Chemical Society, Perkin Transactions 1, 1982, p. 1629-1636 | - |
dc.identifier.issn | 1470-4358 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332793 | - |
dc.description.abstract | The temperature dependences of the <sup>1</sup>H n.m.r. spectra of di-o-thymotide (13) and di-o-carvacrotide (14) have been interpreted in terms of ring inversion (12a) ⇌ (12b) between enantiomeric boat conformations. Comparison of the ΔG<sup>‡</sup>values (17.7 and 18.4 kcal mol<sup>−1</sup>, respectively) for this conformational change suggests that it takes place by a pseudorotational process involving folded boat conformations (17) in which the substituents (methyl and isopropyl, respectively) on C-3 enter into 1,5-interactions with the carbonyl oxygen atoms in the eight-membered rings at the rate-determining transition states. The temperature dependences of the <sup>1</sup>H n.m.r. spectra of tri-o-cresotide (6) and tri-m-cresotide (7) provide further evidence that a mechanism involving pedalling of trans-ester linkages through the mean plane of the twelve-membered ring accounts for the conformational changes between enantiomeric propeller (4) and helical (5) conformations. The ΔG<sup>‡</sup>values for interconversion and inversion processes of eight- and twelve-membered ring compounds show an informative dependence upon the steric demands of the ortho-substituents on the aromatic rings. © 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 9. disalicylides and trisalicylides | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1039/P19820001629 | - |
dc.identifier.scopus | eid_2-s2.0-37049099504 | - |
dc.identifier.spage | 1629 | - |
dc.identifier.epage | 1636 | - |
dc.identifier.isi | WOS:A1982PC03300001 | - |