Abstract
Dihydrogen phosphate selective anion receptors 1, 2, and 3 that utilize amide NH, and CH for anion recognition have been designed and synthesized. For 1 and 2, aromatic CH hydrogen bonding element is present on naphthyl rings (H a). In addition, for receptor 1, this aromatic hydrogen bonding element is further polarized by the nitro groups, which would enhance the hydrogen bonding ability. Partial charges derived from Natural Population Analysis also supported the existence of this polarization. That is, positive partial charge of H a in receptor 1 was more positive than that in receptor 2. As expected from the partial charge values, receptor 1 consistently showed highest affinity among three receptors, followed by receptor 2 regardless of the anions tested in this study. Therefore, we have shown that affinity modulation of a receptor was possible by changing the nature of the aromatic CH hydrogen. In addition, the receptors showed selectivity toward dihydrogen phosphate among various anions including acetate and chloride.
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