A Lewis acid-mediated conformational switch.
Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis and conformational behaviour of an isonicotinamide-substituted diphenylacetylene up...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Royal Society of Chemistry
2014
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| _version_ | 1797058136529436672 |
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| author | Knipe, P Lingard, H Jones, I Thompson, S Hamilton, A |
| author_facet | Knipe, P Lingard, H Jones, I Thompson, S Hamilton, A |
| author_sort | Knipe, P |
| collection | OXFORD |
| description | Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis and conformational behaviour of an isonicotinamide-substituted diphenylacetylene upon recognition of Lewis acids, including metalloporphyrins. Binding of these at a remote site - the pyridyl nitrogen - increases hydrogen-bond donor ability of the proximal amide NH, causing an increased preference for the alkyne rotamer in which this hydrogen bond is maintained. |
| first_indexed | 2024-03-06T19:46:16Z |
| format | Journal article |
| id | oxford-uuid:2267ac6f-961e-4304-b2cd-2ee493b5ce1f |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:46:16Z |
| publishDate | 2014 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:2267ac6f-961e-4304-b2cd-2ee493b5ce1f2022-03-26T11:38:44ZA Lewis acid-mediated conformational switch.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:2267ac6f-961e-4304-b2cd-2ee493b5ce1fEnglishSymplectic Elements at OxfordRoyal Society of Chemistry2014Knipe, PLingard, HJones, IThompson, SHamilton, AMolecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis and conformational behaviour of an isonicotinamide-substituted diphenylacetylene upon recognition of Lewis acids, including metalloporphyrins. Binding of these at a remote site - the pyridyl nitrogen - increases hydrogen-bond donor ability of the proximal amide NH, causing an increased preference for the alkyne rotamer in which this hydrogen bond is maintained. |
| spellingShingle | Knipe, P Lingard, H Jones, I Thompson, S Hamilton, A A Lewis acid-mediated conformational switch. |
| title | A Lewis acid-mediated conformational switch. |
| title_full | A Lewis acid-mediated conformational switch. |
| title_fullStr | A Lewis acid-mediated conformational switch. |
| title_full_unstemmed | A Lewis acid-mediated conformational switch. |
| title_short | A Lewis acid-mediated conformational switch. |
| title_sort | lewis acid mediated conformational switch |
| work_keys_str_mv | AT knipep alewisacidmediatedconformationalswitch AT lingardh alewisacidmediatedconformationalswitch AT jonesi alewisacidmediatedconformationalswitch AT thompsons alewisacidmediatedconformationalswitch AT hamiltona alewisacidmediatedconformationalswitch AT knipep lewisacidmediatedconformationalswitch AT lingardh lewisacidmediatedconformationalswitch AT jonesi lewisacidmediatedconformationalswitch AT thompsons lewisacidmediatedconformationalswitch AT hamiltona lewisacidmediatedconformationalswitch |