SYNTHESIS AND COMPLEXATION PROPERTIES OF A NOVEL POTASSIUM-SELECTIVE TRISANISYL BIS(BENZO-CROWN ETHER)
The condensation of 2,2′2″-trimethoxy-5,5′,5″- trimethyl-1,1′:3′,1″-terphenyl-3,3″-di(carbonyl chloride) (2) with two equivalents of 4-aminobenzo-15-crown-5 (15-amino-2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine) (3) gave a novel bis(crown ether) (4) containing a rigid preor...
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| Format: | Journal article |
| Language: | English |
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1990
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| _version_ | 1797098778323320832 |
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| author | Beer, P Tite, E Ibbotson, A |
| author_facet | Beer, P Tite, E Ibbotson, A |
| author_sort | Beer, P |
| collection | OXFORD |
| description | The condensation of 2,2′2″-trimethoxy-5,5′,5″- trimethyl-1,1′:3′,1″-terphenyl-3,3″-di(carbonyl chloride) (2) with two equivalents of 4-aminobenzo-15-crown-5 (15-amino-2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine) (3) gave a novel bis(crown ether) (4) containing a rigid preorganised trisanisyl chain backbone. Titrations of this new host with alkali-metal cations and the ammonium ion monitored by 13C n.m.r. spectroscopy suggested that the benzo crown ether moieties alone provided the co-ordinating sites for the cationic guests, forming a 1:2 [(4):M+] complex with sodium ions, while potassium, rubidium, and ammonium ions formed 1:1 intramolecular sandwich complexes. The association constants (K/dm3 mol-1) of the bis(crown ether) (4) with picrate salts of potassium (7.93 × 10 6), rubidium (0.19 × 106), caesium (0.03 × 106), and ammonium (0.02 × 106) in CDCl3 were measured by deuteriochloroform-water extraction and spectroscopic techniques, indicating a high degree of selectivity for potassium over the other cations [K(K+)/K(Rb+) = 42, K(K+)/K(Cs +) = 264, and K(K+)/K(NH4+) = 397]. This result is in agreement with fast-atom-bombardment mass spectrometric competition experiments. |
| first_indexed | 2024-03-07T05:14:31Z |
| format | Journal article |
| id | oxford-uuid:dcb6dc73-c7ce-4e61-965b-de294e844510 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:14:31Z |
| publishDate | 1990 |
| record_format | dspace |
| spelling | oxford-uuid:dcb6dc73-c7ce-4e61-965b-de294e8445102022-03-27T09:19:32ZSYNTHESIS AND COMPLEXATION PROPERTIES OF A NOVEL POTASSIUM-SELECTIVE TRISANISYL BIS(BENZO-CROWN ETHER)Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:dcb6dc73-c7ce-4e61-965b-de294e844510EnglishSymplectic Elements at Oxford1990Beer, PTite, EIbbotson, AThe condensation of 2,2′2″-trimethoxy-5,5′,5″- trimethyl-1,1′:3′,1″-terphenyl-3,3″-di(carbonyl chloride) (2) with two equivalents of 4-aminobenzo-15-crown-5 (15-amino-2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine) (3) gave a novel bis(crown ether) (4) containing a rigid preorganised trisanisyl chain backbone. Titrations of this new host with alkali-metal cations and the ammonium ion monitored by 13C n.m.r. spectroscopy suggested that the benzo crown ether moieties alone provided the co-ordinating sites for the cationic guests, forming a 1:2 [(4):M+] complex with sodium ions, while potassium, rubidium, and ammonium ions formed 1:1 intramolecular sandwich complexes. The association constants (K/dm3 mol-1) of the bis(crown ether) (4) with picrate salts of potassium (7.93 × 10 6), rubidium (0.19 × 106), caesium (0.03 × 106), and ammonium (0.02 × 106) in CDCl3 were measured by deuteriochloroform-water extraction and spectroscopic techniques, indicating a high degree of selectivity for potassium over the other cations [K(K+)/K(Rb+) = 42, K(K+)/K(Cs +) = 264, and K(K+)/K(NH4+) = 397]. This result is in agreement with fast-atom-bombardment mass spectrometric competition experiments. |
| spellingShingle | Beer, P Tite, E Ibbotson, A SYNTHESIS AND COMPLEXATION PROPERTIES OF A NOVEL POTASSIUM-SELECTIVE TRISANISYL BIS(BENZO-CROWN ETHER) |
| title | SYNTHESIS AND COMPLEXATION PROPERTIES OF A NOVEL POTASSIUM-SELECTIVE TRISANISYL BIS(BENZO-CROWN ETHER) |
| title_full | SYNTHESIS AND COMPLEXATION PROPERTIES OF A NOVEL POTASSIUM-SELECTIVE TRISANISYL BIS(BENZO-CROWN ETHER) |
| title_fullStr | SYNTHESIS AND COMPLEXATION PROPERTIES OF A NOVEL POTASSIUM-SELECTIVE TRISANISYL BIS(BENZO-CROWN ETHER) |
| title_full_unstemmed | SYNTHESIS AND COMPLEXATION PROPERTIES OF A NOVEL POTASSIUM-SELECTIVE TRISANISYL BIS(BENZO-CROWN ETHER) |
| title_short | SYNTHESIS AND COMPLEXATION PROPERTIES OF A NOVEL POTASSIUM-SELECTIVE TRISANISYL BIS(BENZO-CROWN ETHER) |
| title_sort | synthesis and complexation properties of a novel potassium selective trisanisyl bis benzo crown ether |
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