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Phosphinate selective hosts and importance of CH hydrogen bonding for affinity modulation toward anion guests
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2018-03-23 , DOI: 10.1016/j.tetlet.2018.03.066
Dae Hyup Sohn , Eunbi Han , Seung Joo Cho , Jongmin Kang

Even though phosphinate and its analogs are very important guests in nature, the artificial receptors which are capable of selective recognition of phosphinate are rare. Here, we report a series of acetate and phosphinate selective hosts (1, 2 and 3) which utilize amide NH and aliphatic CH groups as hydrogen bonding donors. In this series of receptors, even though the amide NH hydrogen bonding element was found to be the most significant, by varying the polarity of CH group, the magnitude of recognition could be modulated considerably. The affinities of host 3 against all the tested anion guests showed significantly higher affinities compared with those of hosts 1 and 2, and this could be attributed to the difference of CH group polarities among the receptors 1, 2 and 3. Cα-H hydrogen in host 3 is the most highly polarized by the charged pyridinium group. Therefore, it is the strongest host in this series of hosts. From the experiments shown here, we demonstrated the importance of CH hydrogen bonding element as a decisive modulating moiety for anionic recognition.



中文翻译:

膦酸酯的选择性主体和C H氢键对阴离子客体的亲和力调节的重要性

尽管次膦酸盐及其类似物在自然界中是非常重要的客人,但是能够选择性识别次膦酸盐的人工受体却很少。这里,我们报告了一系列乙酸酯和次膦酸酯的选择性主机(的123),其利用酰胺Ñ H和脂族C H基团作为氢键供体。在这一系列受体中,即使发现酰胺N H氢键元素是最重要的,通过改变C H基团的极性,也可以显着调节识别的幅度。与宿主1相比,宿主3对所有测试的阴离子客体的亲和力显示出显着更高的亲和力2,这可以归因于C的差H组极性的受体中123。Ç α在宿主-H氢3是由带电吡啶鎓基高度偏振的最多。因此,它是该系列主机中最强的主机。从此处显示的实验中,我们证明了C H氢键元件作为阴离子识别的决定性调节部分的重要性。

更新日期:2018-03-23
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