Tripodal tris(diamide) receptor having H-bond donors and acceptors on trindane platform for H2PO4− recognition
| Autor: | Shilpa Bothra, Heung-Jin Choi, Suban K. Sahoo, Gi-Dong Kim |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Tris
010405 organic chemistry Hydrogen bond General Chemistry 010402 general chemistry Condensed Matter Physics 01 natural sciences Binding constant Acceptor Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Pyridine Proton NMR Titration Density functional theory Food Science |
| Zdroj: | Journal of Inclusion Phenomena and Macrocyclic Chemistry. 95:215-221 |
| ISSN: | 1573-1111 1388-3127 |
| DOI: | 10.1007/s10847-019-00937-3 |
| Popis: | A new C3v-symmetric tris(diamide) receptor 2 possessing both H-bond donor and acceptor sites was synthesized and characterized by various spectral data. The anion recognition ability of receptor 2 was investigated by 1H NMR in DMSO-d6. Among the tested anions (F−, Cl−, Br−, I−, NO3−, HSO4− and H2PO4−), the receptor 2 shows high selectivity towards H2PO4− anion. The amide-NH protons peaks of receptor 2 at δ 10.42 and δ 8.23 ppm were broadened and shifted to downfield region in the presence of H2PO4−. The appended arms with tris(diamide) H-bond donors and pyridine H-bond acceptors of receptor 2 provide a preorganized cavity to encapsulate the H2PO4− through multiple hydrogen bonds. The 1H NMR titration measures the binding constant (Ka) of 293 M−1 for the host–guest complex formed between receptor 2 and H2PO4−. Further, the possible 3D structure of receptor 2 and its complex with H2PO4− anion was proposed through density functional theory method. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full text from SpringerLink