Halogen bonding molecular capsules
Dumele, O; Trapp, N; Diederich, F
HERO ID
3120753
Reference Type
Journal Article
Year
2015
Language
English
PMID
| HERO ID | 3120753 |
|---|---|
| In Press | No |
| Year | 2015 |
| Title | Halogen bonding molecular capsules |
| Authors | Dumele, O; Trapp, N; Diederich, F |
| Journal | Angewandte Chemie (International Edition) |
| Volume | 54 |
| Issue | 42 |
| Page Numbers | 12339-12344 |
| Abstract | Molecular capsules based solely on the interaction of halogen bonding (XB) are presented along with their host-guest binding properties in solution. The first example of a well-defined four-point XB supramolecular system is realized by decorating resorcin[4]arene cavitands with polarized halogen atoms for dimerization with tetra(4-pyridyl) resorcin[4]arene cavitands. NMR binding data for the F, Cl, Br, and I cavitands as the XB donor show association constants (Ka ) of up to 5370 M(-1) (ΔG283 K =-4.85 kcal mol(-1) , for I), even in XB-competitive solvent, such as deuterated benzene/acetone/methanol (70:30:1) at 283 K, where comparable monodentate model systems show no association. The XB capsular geometry is evidenced by two-dimensional HOESY NMR, and the thermodynamic profile shows that capsule formation is enthalpically driven. Either 1,4-dioxane or 1,4-dithiane are encapsulated within each of the two separate cavities within the XB capsule, with of up to Ka =9.0 10(8) M(-2) (ΔG283 K =-11.6 kcal mol(-1) ). |
| Doi | 10.1002/anie.201502960 |
| Pmid | 26013544 |
| Wosid | WOS:000363397300013 |
| Url | https://www.proquest.com/scholarly-journals/halogen-bonding-molecular-capsules/docview/1718901696/se-2?accountid=171501 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Journal: ISSN: |
| Is Public | Yes |
| Language Text | English |
| Keyword | halogen bonding; host-guest systems; self-assembly; supramolecular chemistry; X-ray diffraction |