Adelaide Research & Scholarship
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https://hdl.handle.net/2440/4695
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| Type: | Journal article |
| Title: | Synthesis and conformational analysis of an a-cyclodextrin [2]-rotaxane |
| Author: | Easton, C. Lincoln, S. Meyer, A. Ongani, H. |
| Citation: | Journal of the Chemical Society. Perkin transactions 1, 1999; (17):2501-2506 |
| Publisher: | ROYAL SOC CHEMISTRY |
| Issue Date: | 1999 |
| ISSN: | 0300-922X 1364-5463 |
| Statement of Responsibility: | Christopher J. Easton, Stephen F. Lincoln, Adam G. Meyer and Hideki Onagi |
| Abstract: | An a-cyclodextrin [2]-rotaxane has been prepared in 10% yield, by threading a-cyclodextrin (a-CD) with (£)-4, 4'diaminostilbene in aqueous solution and capping the included guest through reaction with 2, 4, 6-trinitrobenzene-lsulfonate. ID 'H NMR spectroscopy and DQCOSY and ROES Y experiments show that the a-CD rotates freely around the axle of the rotaxane, but is localised over the olefinic moiety of the stilbene. The pA"a values of the a-CD [2]-rotaxane were found to be 9.3 and 9.6, which are attributable to deprotonations of the (£')-4)4'-bis(2, 4, 6-trinitrophenylamino)stilbene moiety. NMR experiments show that these deprotonations do not perturb the conformation of the rotaxane. |
| DOI: | 10.1039/a902176k |
| Published version: | http://dx.doi.org/10.1039/a902176k |
| Appears in Collections: | Aurora harvest 6 Chemistry publications Environment Institute publications |
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