A Bis-Crown Ether Derivative of Triaminotriazine: Synthesis and Behavior of the Ion-Selective and Hydrogen-Bonding Responsive Rotamers
作者： Joe Otsuki , Keith C. Russell , Jean-Marie Lehn
DOI: 10.1246/BCSJ.70.671
关键词: Crystallography 、 Phthalic acid 、 Conformational isomerism 、 Hydrogen bond 、 Proton NMR 、 Triazine 、 Chemistry 、 Ether 、 Crown ether 、 Derivative (chemistry)
摘要: A bis-crown ether derivative of triaminotriazine was synthesized via a phthalic acid polyether macrocycle obtained from benzo-18-crown-6. It exists in different conformers distinguishable by 1H NMR at room temperature, which the macrocyclic side-arms take closed, half-open, or fully open form, due to rotational barrier C(triazine)–N bond. Large alkali metal ions, such as Rb+ and Cs+, latter being particularly effective, promote formation closed conformer. barbiturate also causes similar equilibrium shift form establishing complementary hydrogen bonds. The half-open are induced smaller ions than Rb+, among K+ is most effective.
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