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Bisamides derived from azulene-1,3-and-5,7-dicarboxylic acids as new building blocks for anion receptors

机译:衍生自Azulene-1,3-和-5,7-二羧酸的双酰胺类化合物作为阴离子受体的新组成部分

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摘要

Bisamides based on the azulene moiety were investigated as building blocks for anion receptors. In the course of these studies, derivatives of azulene-1,3- and -5,7-dicarboxylic acid were synthesized and thoroughly characterized. The anion affinities of the derivatives based on functionalization in the five-membered ring and in the seven-membered ring were determined by H-1 NMR titration. The structural analysis of these building, blocks was performed by X-ray diffractometry, molecular modelling and 2D NMR spectroscopy. The five-membered ring derivatives are easy to obtain, offer a binding site preorganized in the syn-syn conformation and bind anions with a strength similar to those of pyrrole-based analogues. There is also strong evidence for aromatic CH center dot center dot center dot anion interactions. The ligands substituted at the 5- and 7-positions offer a binding cleft with an uncommon geometry that originates from the seven-membered ring and seems to be complementary to the chloride anion.
机译:研究了基于z基部分的双酰胺作为阴离子受体的组成部分。在这些研究过程中,合成并详细表征了azulene-1,3-和-5,7-二羧酸衍生物。通过H-1 NMR滴定确定基于五元环和七元环中官能化的衍生物的阴离子亲和力。这些结构单元的结构分析是通过X射线衍射,分子建模和2D NMR光谱进行的。五元环衍生物易于获得,提供了以syn-syn构象预组织的结合位点,并以类似于基于吡咯的类似物的强度结合了阴离子。也有很强的证据表明芳香族CH中心点中心点中心点阴离子之间的相互作用。在5位和7位上取代的配体提供了具有不常见几何形状的结合裂隙,该裂隙起源于七元环,似乎与氯离子互补。

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