Host-guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies.

ABSTRACT: Host-guest complexes of C-hexyl-2-bromoresorcinarene (BrC6) with twelve potential aromatic N-oxide guests were studied using single crystal X-ray diffraction analysis and 1H NMR spectroscopy. In the solid state, of the nine obtained X-ray crystal structures, eight were consistent with the formation of BrC6-N-oxide endo complexes. The lone exception was from the association between 4-phenylpyridine N-oxide and BrC6, in that case the host forms a self-inclusion complex. BrC6, as opposed to more rigid previously studied C-ethyl-2-bromoresorcinarene and C-propyl-2-bromoresorcinarene, undergoes remarkable cavity conformational changes to host different N-oxide guests through C-H···π(host) interactions. In solution phase CD3OD/CDCl3 (1:1 v/v), all twelve N-oxide guests form endo complexes accord

SUBMITTER: Puttreddy R 

PROVIDER: S-EPMC6071688 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature