Macrocyclic bis(ureas) as ligands for anion complexation
Two macrocyclic bis(ureas) 1 and 2, both based on diphenylurea, have been synthesized. Compound 1 represents the smaller ring with two ethynylene groups as linkers and 2 the larger ring with two butadiynylene groups. On thermal treatment to 130 °C molecule 1 splits up into two dihydroindoloquinolino...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-08-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.193 |
| _version_ | 1818447643492220928 |
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| author | Claudia Kretschmer Gertrud Dittmann Johannes Beck |
| author_facet | Claudia Kretschmer Gertrud Dittmann Johannes Beck |
| author_sort | Claudia Kretschmer |
| collection | DOAJ |
| description | Two macrocyclic bis(ureas) 1 and 2, both based on diphenylurea, have been synthesized. Compound 1 represents the smaller ring with two ethynylene groups as linkers and 2 the larger ring with two butadiynylene groups. On thermal treatment to 130 °C molecule 1 splits up into two dihydroindoloquinolinone (3) molecules. Both compounds 1 and 2 form adducts with polar molecules such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF) and act as complexing agents towards a series of anions (Cl−, Br−, I−, NO3−, HSO4−). The crystal structures of 3, 2·2DMSO, 2·2DMF, and of the complex NEt4[Br·2] have been determined. Quantitative investigations of the complexation equilibria were performed via 1H NMR titrations. While 1 is a rather weak complexing agent, the large ring of 2 binds anions with association constants up to log K = 7.93 for chloride ions. |
| first_indexed | 2024-12-14T20:06:53Z |
| format | Article |
| id | doaj.art-3a75a2b4060844c298fe8ee4d5a60d78 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T20:06:53Z |
| publishDate | 2014-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-3a75a2b4060844c298fe8ee4d5a60d782022-12-21T22:49:01ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-08-011011834183910.3762/bjoc.10.1931860-5397-10-193Macrocyclic bis(ureas) as ligands for anion complexationClaudia Kretschmer0Gertrud Dittmann1Johannes Beck2Institute for Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, GermanyInstitute for Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, GermanyInstitute for Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, GermanyTwo macrocyclic bis(ureas) 1 and 2, both based on diphenylurea, have been synthesized. Compound 1 represents the smaller ring with two ethynylene groups as linkers and 2 the larger ring with two butadiynylene groups. On thermal treatment to 130 °C molecule 1 splits up into two dihydroindoloquinolinone (3) molecules. Both compounds 1 and 2 form adducts with polar molecules such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF) and act as complexing agents towards a series of anions (Cl−, Br−, I−, NO3−, HSO4−). The crystal structures of 3, 2·2DMSO, 2·2DMF, and of the complex NEt4[Br·2] have been determined. Quantitative investigations of the complexation equilibria were performed via 1H NMR titrations. While 1 is a rather weak complexing agent, the large ring of 2 binds anions with association constants up to log K = 7.93 for chloride ions.https://doi.org/10.3762/bjoc.10.193anion bindingmacrocyclic compoundsNMR spectrasupramolecular chemistrytemplateurea |
| spellingShingle | Claudia Kretschmer Gertrud Dittmann Johannes Beck Macrocyclic bis(ureas) as ligands for anion complexation Beilstein Journal of Organic Chemistry anion binding macrocyclic compounds NMR spectra supramolecular chemistry template urea |
| title | Macrocyclic bis(ureas) as ligands for anion complexation |
| title_full | Macrocyclic bis(ureas) as ligands for anion complexation |
| title_fullStr | Macrocyclic bis(ureas) as ligands for anion complexation |
| title_full_unstemmed | Macrocyclic bis(ureas) as ligands for anion complexation |
| title_short | Macrocyclic bis(ureas) as ligands for anion complexation |
| title_sort | macrocyclic bis ureas as ligands for anion complexation |
| topic | anion binding macrocyclic compounds NMR spectra supramolecular chemistry template urea |
| url | https://doi.org/10.3762/bjoc.10.193 |
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