aromatic N-oxides, crystal structure, hydrogen bonds, resorcinarenes, Supramolecular chemistry
The host-guest complexes of C-propyl-2-bromoresorcinarene with pyridine N-oxide, 3-methylpyridine N-oxide, quinoline N-oxide and isoquinoline N-oxide are studied using single crystal X-ray crystallography and 1H NMR spectroscopy. The C-propyl-2-bromoresorcinarene forms endo-complexes with the aromatic N-oxides in the solid-state when crystallised from either methanol or acetone. In solution, the endo-complexes were observed only in methanol-d4. In DMSO the solvent itself is a good guest, and crystallisation provides only solvate endo-complexes. The C-propyl-2-bromoresorcinarene shows remarkable flexibility when crystallised from either methanol or acetone, and packs into one-dimensional self-included chains. Of special note, crystallising C-propyl-2-bromoresorcinarene with 3-methylpyridine N-oxide from acetone results in a 2:2 dimeric capsular assembly organised through both C−H···πhost and N−O···(H−O)host interactions.
Puttreddy, Rakesh; Beyeh, Ngong Kodiah; Jurček, Pia; Turunen, Lotta; Trant, John F.; Ras, Robin H.A.; and Rissanen, Kari. (2018). Host-guest complexes of C-propyl-2-bromoresorcinarene with aromatic N-oxides*. Supramolecular Chemistry, 30 (5-6), 445-454.