期刊名称:Proceedings of the National Academy of Sciences
印刷版ISSN:0027-8424
电子版ISSN:1091-6490
出版年度:2002
卷号:99
期号:8
页码:4842-4847
DOI:10.1073/pnas.062625499
语种:English
出版社:The National Academy of Sciences of the United States of America
摘要:Two neutral macrobicyclic anion receptors 4 and 6, containing a calix[4]arene in the cone conformation, two L-alanine units, and a 2,6-diacylpyridine or a phthaloyl bridge, are described. The x-ray crystal structure of the acetone complexes of the pyridine containing macrocycle 6 shows the four amide NH groups to be in close proximity to the chiral pocket delimited by the pyridine and one aromatic nucleus of the calix[4]arene. This conformation is also the most stable in acetone-d6 solution, as proven by one- and two-dimensional NMR spectral measurements. Electrospray ionization-MS and 1H NMR experiments reveal that the two ligands strongly bind carboxylate anions in acetone solution. H-bonding interactions between the carboxylate anions and the amide NH groups, together with {pi}/{pi} stacking, are invoked to explain the efficiency and the selectivity of these anion receptors.