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首页> 外文期刊>Chemistry: A European journal >Dimeric self-assembly of pyridyl guanidinium carboxylates in polar solvents
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Dimeric self-assembly of pyridyl guanidinium carboxylates in polar solvents

机译：极性溶剂中吡啶基吡啶鎓羧酸盐的二聚体自组装

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摘要

A series of pyridyl guanidinium-carboxylates has been prepared and the dimeric self-assembly of these studied in H_2O/DMSO mixtures, principally using dilution isothermal calorimetry. Compounds 5 and 6, incorporating an aromatic ring in the "tethering" region between the guanidinium and carboxylate groups, demonstrate the strongest dimerisation in neat DMSO. X-ray crystal structures of 5 and 6 reveal two different dimerisation architectures in the solid-state, but both involve carboxylate-guanidinium salt bridges as anticipated, and π-π interactions. Compounds 10-16 incorporating peptidic fragments between the guanidinium and carboxylate groups, showed reduced dimerisation strength with increased amino acid content, but also sustained dimerisation under increasingly aqueous conditions, up to 50% H_2O/DMSO in the case of 14 and 15. The extent of our study in H _2O/DMSO mixtures was determined by substrate solubility of 10-16, and not the limit of self-assembly. Pairing up: A dimeric self-assembly of pyridyl guanidinium carboxylates (see scheme) has been conceived as a simple model for characterisation of intermolecular interactions between a variable tethering region. We describe the synthesis and study of the self-assembly in H _2O/DMSO solvent systems using dilution microcalorimetry and ~1H NMR spectroscopy.
机译：已经制备了一系列吡啶基胍盐-羧酸盐，并且主要使用稀释等温量热法在H_2O / DMSO混合物中研究了它们的二聚体自组装。化合物5和6在胍基和羧酸酯基团之间的“束缚”区域掺入了芳环，在纯DMSO中显示出最强的二聚作用。 5和6的X射线晶体结构在固态下显示出两种不同的二聚结构，但正如预期的那样，它们都涉及羧酸盐-胍盐桥和π-π相互作用。在胍基和羧酸酯基团之间掺入肽片段的化合物10-16表现出降低的二聚强度，同时增加了氨基酸含量，而且在不断增加的水性条件下也持续存在二聚作用，在14和15的情况下，最高可达50％H_2O / DMSO。我们在H _2O / DMSO混合物中的研究结果是由10-16的底物溶解度决定的，而不是自组装的极限。配对：吡啶基吡啶鎓羧酸盐的二聚体自组装体（参见方案）被认为是表征可变束缚区之间分子间相互作用的简单模型。我们描述了使用稀释微量量热法和〜1H NMR光谱在H _2O / DMSO溶剂系统中自组装的合成和研究。

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