Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes
The syntheses and single crystal X-ray structure determinations of 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(cyanomethoxy)calix[4]arene (partial-cone conformer), 5,11,17,23-tetra-tert-butyl-25,27-bis(diethylcarbamoylmethoxy)-26,28-bis(cyanomethoxy)calix[4]arene (cone and partial-cone conforme...
| Main Authors: | , , , , , |
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| Format: | Journal Article |
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Royal Society of Chemistry
2016
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| Online Access: | http://hdl.handle.net/20.500.11937/38951 |
| _version_ | 1848755458332950528 |
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| author | D'Alessio, D. Krause-Heuer, A. Skelton, B. Fraser, B. Massi, Massimiliano Ogden, Mark |
| author_facet | D'Alessio, D. Krause-Heuer, A. Skelton, B. Fraser, B. Massi, Massimiliano Ogden, Mark |
| author_sort | D'Alessio, D. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | The syntheses and single crystal X-ray structure determinations of 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(cyanomethoxy)calix[4]arene (partial-cone conformer), 5,11,17,23-tetra-tert-butyl-25,27-bis(diethylcarbamoylmethoxy)-26,28-bis(cyanomethoxy)calix[4]arene (cone and partial-cone conformers), 5,11,17,23-tetra-tert-butyl-25,26,27-tris(cyanomethoxy)-28-hydroxycalix[4]arene, and 5,11,17,23-tetra-tert-butyl-25-diethylcarbamoylmethoxy-26,27,28-tris(cyanomethoxy)calix[4]arene (cone conformer) are reported. The calixarenes are found to be conformationally mobile when heated in DMSO, favouring the partial-cone conformer at equilibrium. The tris-substituted cyanomethoxy derivative was found to assume the partial-cone conformation in the solid state. Attempts to convert nitrile groups to tetrazole moieties in derivatives containing both amide and nitrile groups were unsuccessful. |
| first_indexed | 2025-11-14T08:56:37Z |
| format | Journal Article |
| id | curtin-20.500.11937-38951 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T08:56:37Z |
| publishDate | 2016 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-389512017-09-13T14:22:14Z Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes D'Alessio, D. Krause-Heuer, A. Skelton, B. Fraser, B. Massi, Massimiliano Ogden, Mark The syntheses and single crystal X-ray structure determinations of 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(cyanomethoxy)calix[4]arene (partial-cone conformer), 5,11,17,23-tetra-tert-butyl-25,27-bis(diethylcarbamoylmethoxy)-26,28-bis(cyanomethoxy)calix[4]arene (cone and partial-cone conformers), 5,11,17,23-tetra-tert-butyl-25,26,27-tris(cyanomethoxy)-28-hydroxycalix[4]arene, and 5,11,17,23-tetra-tert-butyl-25-diethylcarbamoylmethoxy-26,27,28-tris(cyanomethoxy)calix[4]arene (cone conformer) are reported. The calixarenes are found to be conformationally mobile when heated in DMSO, favouring the partial-cone conformer at equilibrium. The tris-substituted cyanomethoxy derivative was found to assume the partial-cone conformation in the solid state. Attempts to convert nitrile groups to tetrazole moieties in derivatives containing both amide and nitrile groups were unsuccessful. 2016 Journal Article http://hdl.handle.net/20.500.11937/38951 10.1039/c6ra05865e Royal Society of Chemistry fulltext |
| spellingShingle | D'Alessio, D. Krause-Heuer, A. Skelton, B. Fraser, B. Massi, Massimiliano Ogden, Mark Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes |
| title | Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes |
| title_full | Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes |
| title_fullStr | Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes |
| title_full_unstemmed | Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes |
| title_short | Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes |
| title_sort | synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes |
| url | http://hdl.handle.net/20.500.11937/38951 |