Inclusion of 1,8-octanediphosphonic acid in cucurbit[7]uril: a combined solid state and solution study

IF 2.3 4区化学 Q2 Agricultural and Biological Sciences Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-03-19 DOI:10.1007/s10847-024-01227-3

Marina Cagnes, Inna Karatchevtseva, Alexander Angeloski, Yingjie Zhang

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Abstract

The inclusion of 1,8-octanediphosphonic acid (OA) in cucurbit[7]uril (Q[7]) has been investigated via a combined solid state and solution study. The reaction of OA and Q[7] in water led to the formation of a 1:1 inclusion compound 1 as a white crystalline material. Synchrotron single crystal X-ray diffraction revealed its detailed structure validated by Raman spectroscopy with featured vibrational modes from both organic molecules. Subsequent ¹H solution NMR data supported the formation of a 1:1 inclusion complex in aqueous solution. The changes in NMR chemical shifts are consistent with the solid-state orientation in which the phosphonic acid groups of OA are oriented externally to the carbonyl portals and the intervening alkyl chain lies within the cavity of Q[7]. However, the solution study also inferred possible formations of other complexes in solution. This work highlighted the advantage of combining solid state and solution studies to reveal the detailed molecular interactions involving complex inclusion phenomena.

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葫芦[7]脲中的 1,8-辛二膦酸：固态和溶液综合研究

通过固态和溶液联合研究，对葫芦[7]脲（Q[7]）中的 1,8-辛二膦酸（OA）包合物进行了调查。OA 和 Q[7] 在水中反应生成了 1:1 的包合物 1，呈白色结晶状。同步辐射单晶 X 射线衍射显示了它的详细结构，并通过拉曼光谱验证了这两种有机分子的特征振动模式。随后的 1H 溶液 NMR 数据支持在水溶液中形成 1:1 的包合物复合物。核磁共振化学位移的变化与固态取向一致，即 OA 的膦酸基团位于羰基门户的外部，而中间的烷基链位于 Q 的空腔内[7]。不过，溶液研究也推断出在溶液中可能形成其他复合物。这项工作凸显了结合固态和溶液研究来揭示涉及复杂包涵现象的详细分子相互作用的优势。

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来源期刊

Journal of Inclusion Phenomena and Macrocyclic Chemistry 化学-化学综合

CiteScore

3.30

自引率

8.70%

发文量

审稿时长

3-8 weeks

期刊介绍： The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.