Exploring structural and conformational behaviour of cyclophanes incorporating imidazole-2-thiones |
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Authors: | Ahmed H Mageed Brian W Skelton Alexandre N Sobolev Murray V Baker |
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Institution: | 1. School of Molecular Sciences M310, The University of Western Australia, 35 Stirling Highway, Perth, WA, 6009, Australia;2. Department of Chemistry, Faculty of Science, University of Kufa, P.O. Box 21, An-Najaf, 54001, Iraq;3. Centre for Microscopy, Characterisation and Analysis M310, The University of Western Australia, Perth, WA, 6009, Australia |
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Abstract: | New cyclophanes containing two imidazole-2-thione moieties linked by two xylylene groups have been synthesized by the reaction of imidazolium-linked cyclophanes with sulfur in the presence of K2CO3. The conformational behaviour of the new cyclophanes was explored by NMR spectroscopy and X-ray diffraction studies. In cyclophanes containing o-xylylene or 2,4,6-trimethyl-m-xylylene linking groups, the imidazole-2-thione groups were mutually syn in both the solid state and in solution, the cyclophanes adopting a conformation reminiscent of the cone conformation of calix4]arenes. Cyclophanes containing p-xylylene or m-xylylene linking groups exhibited two conformations in solution, one in which the imidazole-2-thione groups are mutually syn, the other in which they are mutually anti, and these conformations did not interconvert on the NMR timescale. Both conformations co-crystallised in the m-xylylene linked cyclophane, while for the p-xylylene-linked cyclophane the anti conformation crystallised separately. |
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Keywords: | Imidazole-2-thiones Cyclophanes Conformations Imidazolium salts |
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