879218-32-3Relevant academic research and scientific papers
Is [N+-H...O] hydrogen bonding the most important noncovalent interaction in macrocycle-dibenzylammonium ion complexes?
Cheng, Pin-Nan,Huang, Po-Yi,Li, Wan-Sheung,Ueng, Shau-Hua,Hung, Wei-Chung,Liu, Yi-Hung,Lai, Chien-Chen,Wang, Yu,Peng, Shie-Ming,Chao, Ito,Chiu, Sheng-Hsien
, p. 2373 - 2383 (2006)
We report a new host molecule in which one diethylene glycol chain (i.e., a loop possessing only three oxygen atoms) incorporated along with two phenolic aromatic rings is linked by a xylene spacer into a macroring. The design of the molecular structure of this macrocycle "amplifies" any potential [cation...π], [N+-H...π], and [N+C- H...π] interactions between the dibenzylammonium (DBA+) ion and the phenolic rings of the macrocycle; as such, these species display a very strong binding affinity in CD3NO2 (Ka = 15 000 M-1). The macroring also coordinates to bipyridinium ions in a [2]pseudorotaxane fashion, which makes it the smallest macrocycle (i.e., a 25-membered ring) known to complex both DBA+ and bipyridinium ions in solution. To confirm unambiguously that these pseudorotaxanes exist in solution, we synthesized their corresponding interlocked molecules, namely rotaxanes and catenanes.
