A series of novel hybride chiral macrocyclic compounds is described. The macrocyclic core of the new compounds is decorated with monoterpene fragments and includes 2 imine nitrogens and 2 tertiary amine nitrogens of the N,N-piperazine linkage as well as several repeating ethyleneoxy units resembling those of crown ethers. The macrocyclic compounds are prepared in moderate preparative yield (16–31%) upon treatment of a mixture of bis(α-amine oximes) and α,ω-dichloro derivatives of tri-, tetra- and hexa-ethylene glycol with sodium methylsulfinylmethylide. Chemical structure of the new macrocycles was established by a complex of spectroscopic techniques and X-ray analysis. The new macrocyclic compounds demonstrate remarkable selectivity with respect to Pd(II) and Au(III) and are able to efficiently extract these metals from acidic media containing a complex mixture of alkali metals, 3-elements and noble metals. The features of conformational behavior, the ability to form complexes and the selectivity of extraction were studied using quantum chemical calculations at the DFT level. Based on the data obtained, a consistent scheme has been formulated to explain the features of extraction and the extraction selectivity of individual macrocycles.

中文翻译：

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手性杂化氮杂氧杂萜大环化合物作为 Pd(II) 和 Au(III) 的选择性萃取剂

描述了一系列新型杂化手性大环化合物。新化合物的大环核心用单萜片段装饰，包括N,N-哌嗪键的2个亚胺氮和2个叔胺氮以及几个类似于冠醚的重复乙烯氧基单元。用甲基亚磺酰基甲基化钠处理双（α-胺肟）和三乙二醇、四乙二醇和六乙二醇的α,ω-二氯衍生物的混合物，可以制备出中等收率（16-31%）的大环化合物。通过综合光谱技术和 X 射线分析确定了新大环化合物的化学结构。新的大环化合物对 Pd(II) 和 Au(III) 表现出显着的选择性，并且能够从含有碱金属、三元素和贵金属的复杂混合物的酸性介质中有效地萃取这些金属。利用DFT水平的量子化学计算研究了构象行为的特征、形成复合物的能力和萃取的选择性。根据获得的数据，制定了一致的方案来解释单个大环的提取特征和提取选择性。