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- Publisher Website: 10.1039/P19820001715
- Scopus: eid_2-s2.0-37049108435
- WOS: WOS:A1982PC03300005
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Article: Conformational behaviour of medium-sized rings. Part 13. 5,18- dihydro- and 5,11,12,18-tetrahydrotribenzo[b, f, j][1,4]diazacyclodode- cine-6,17-diones
Title | Conformational behaviour of medium-sized rings. Part 13. 5,18- dihydro- and 5,11,12,18-tetrahydrotribenzo[b, f, j][1,4]diazacyclodode- cine-6,17-diones |
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Authors | |
Issue Date | 1982 |
Citation | Journal of the Chemical Society, Perkin Transactions 1, 1982, p. 1715-1720 How to Cite? |
Abstract | The unsaturated (3) and saturated (6) bislactams have been prepared from condensations of o-phenylenediamine with the bisacyl chlorides (1) and (2) derived from trans-stilbene-2,2′-dicarboxylic acid and bibenzyl-2,2′- dicarboxylic acid, respectively. Dynamic1H n.m.r. spectroscopy demonstrates that the 5,18-dibenzyl derivative (5) of (3) and the 5,18-dimethyl- (7) and 5,18 -dibenzyl- (8) derivatives of (6) adopt enantiomeric non-planar conformations with averaged C |
Persistent Identifier | http://hdl.handle.net/10722/332803 |
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 | 2023-10-06T05:14:24Z | - |
dc.date.available | 2023-10-06T05:14:24Z | - |
dc.date.issued | 1982 | - |
dc.identifier.citation | Journal of the Chemical Society, Perkin Transactions 1, 1982, p. 1715-1720 | - |
dc.identifier.issn | 1470-4358 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332803 | - |
dc.description.abstract | The unsaturated (3) and saturated (6) bislactams have been prepared from condensations of o-phenylenediamine with the bisacyl chlorides (1) and (2) derived from trans-stilbene-2,2′-dicarboxylic acid and bibenzyl-2,2′- dicarboxylic acid, respectively. Dynamic<sup>1</sup>H n.m.r. spectroscopy demonstrates that the 5,18-dibenzyl derivative (5) of (3) and the 5,18-dimethyl- (7) and 5,18 -dibenzyl- (8) derivatives of (6) adopt enantiomeric non-planar conformations with averaged C<inf>2</inf> symmetry in solution. In the case of the two 5,18-dibenzyl derivatives (5) and (8), ring inversion is shown to be slow (ΔG‡ = 20.4 and 21.1 kcal mol<sup>−1</sup>, respectively) on the<sup>X</sup>H n.m.r. time scale at room temperature and probably involves propeller-like conformations (9a) ⇋ (9b) as the enantiomeric ground- state conformations. Both the 5,18-dimethyl- (7) and -dibenzyl (8) derivatives of the saturated bislactam (6) form 1:1 inclusion compounds, (7) with o-xylene and (8) with ethanol. © 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 13. 5,18- dihydro- and 5,11,12,18-tetrahydrotribenzo[b, f, j][1,4]diazacyclodode- cine-6,17-diones | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1039/P19820001715 | - |
dc.identifier.scopus | eid_2-s2.0-37049108435 | - |
dc.identifier.spage | 1715 | - |
dc.identifier.epage | 1720 | - |
dc.identifier.isi | WOS:A1982PC03300005 | - |