機能性ホスト化合物の分子設計と有機化学への応用 : (第2報)機能性カリックスレゾルシン[4]アレーン誘導体の分子認識能と包接挙動について

概要

論文の詳細を見る
Recently, Cation-π interaction has been elucidated to play an important role in many molecular interactions. In this report, the inclusion phenomena of calixresorcin [4] arenes through cation-π interaction is described. The molecular interaction of various substituted (C-and O-) calixresorcin [4] arenes (host) with quarternary ammonium cations, such as N-methyl pyridinium iodide, N-methyl quinolinium iodine and Octyl trimethyl ammonium bromide (guest), has been studied through NMR measurement. C-alkyl, especially cyclohexyl substituted host, showed considerably large chemical shift change of guest molecule to higher field, whereas C-phenyl substituted host gave small effect. The effect of C-substituents may reflect the flextibility of the host molecule to form inclusion complexes by induced-fit mechanisim. All-cis stereoisomer showed effective interaction, but cis-trans isomer shoued small effect. Boat-type conformation of all-cis isomer make cone-type easily to produce effective interaction, whereas chair-type conformation of cis-trans isomer has difficulty to do such interaction. Nuclear Overhauser effect was observed for C-ethyl calix [4] resorcinarene with N-methyl pyridinium iodide.
久留米工業大学の論文
2000-12-20