Kemp's triacid attached to octa-O-methyl resorc[4]arenes: conformations in solution and comparative binding studies with various 2-amino pyridines

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• 作者：Ion Stoll ; Andreas Mix ; Alex ; er B. Rozhenko ; Beate Neumann ; Hans-Georg Stammler ; Jochen Mattay
• 关键词：Calixarenes ; Supramolecular chemistry ; 2-Amino pyridine ; Hydrogen bonds
• 刊名：Tetrahedron
• 出版年：2008
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：21 April 2008
• 卷：64
• 期：17
• 页码：3813-3825
• 文件大小：974 K

摘要

We synthesized the new supramolecular host molecules 7 and 13 based on functionalized resorcarenes bearing Kemp's triacid. Conformations in solution have been investigated and the influence of intra- and intermolecular hydrogen bonds from the triacid was shown by low temperature and DOSY NMR experiments. The results of host 7 are supported by DFT calculations. The binding behaviour of 7 towards different 2-amino pyridines in chloroform has been investigated by NMR titrations. The association constants reach from K=207 M⁻¹ for 2-amino-5-cyano pyridine to K=1551 M⁻¹ for 2-amino-4-methyl pyridine. The association constants of the formed complexes of 7 with 2-amino pyridines were compared with those of the simple host systems 14 and 15 in order to evaluate the influence of the attached resorcarene host.