Computational Analysis of the Nature and Strength of the Supramolecular Contacts Involved in the Binding of Chloride Anions by Imidazolium-Based Cyclic Receptors

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• 作者：Juan Sanz Garc铆a ; Laura Rodr铆guez ; Patrick Gamez ; Arturo Robertazzi
• 刊名：The Journal of Physical Chemistry A
• 出版年：2012
• 出版时间：September 13, 2012
• 年：2012
• 卷：116
• 期：36
• 页码：9110-9115
• 全文大小：247K
• 年卷期：v.116,no.36(September 13, 2012)
• ISSN：1520-5215

文摘

The supramolecular bonding contacts driving the recognition of chloride ions by macrocyclic imidazolium-based receptors have been investigated by density functional theory calculations, both in vacuo and in solution (DMSO). This computational study reveals that the most stable host鈥揼uest complexes in vacuo and solution are different. While the anion interacts by means of two C鈥揌路路路Cl^{鈥?/sup> hydrogen bonds with the host molecule in vacuo (in a similar manner to that observed in the published single-crystal X-ray structure of the Cl鈥揾ost complex), four C鈥揌路路路Cl鈥?/sup> contacts are clearly present in solution, as observed experimentally by earlier studies. In addition, the computed optimal Cl鈥揾ost complex in solution confirms that the cavity of the host macrocycle, formed by four aromatic rings, does not includes the anions, which are located outside the cyclic receptor with which they interact through two C_Ph鈥揌路路路Cl鈥?/sup> hydrogen bonds and two unconventional (C_Im鈥揌)+路路路X鈥?/sup> interactions.}