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A part of a continual sequence, this quantity contains essays on molecular clips and cages derived from glycoluril, concave acids and bases, the molecular attractiveness of natural acids and anions, and molecular acceptance via huge hydrophobic cavities embedded in artificial bilayer membranes.
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Additional info for Supramolecular Chemistry II - Host Design and Molecular Recognition
Surface Studies . . . . ' ....................... 4 Reactions . . . . . . . . . . . . . . . . . . . 1 M o d e l Reactions wilh C o n c a v e Acids . . . . . . . . . 1 The Soft Nef-Reacfion . . . . . . . . . . . . 62 62 65 65 67 67 69 70 71 72 72 73 75 75 77 78 78 78 Topics in Current Chemisty,Vol.
G. see Scheme 2). These reactions have remarkably high yields (up to 75%) for closure of 22- to 25-membered rings. Presumably a template effect of the cation of the base used in the reaction is operative. Basket compounds with a nitrogen atom in the crown ether moieties are most conveniently synthesized by the route depicted in Scheme 3 . With this method even higher yields (up to 89%) were obtained in the ring closure steps. Using similar routes, the chiral baskets 20-22 were also prepared.
As a first step toward a dopamine-fl-hydroxylase mimic, basket-shaped receptor 17 was functionalized with two sets of bis-[2-(3,5-dimethyl-l-pyrazolyl)ethyl]amine ligands to give compound 35 (see Scheme 5). 6H20 yielded complex 36 which was fully characterized . Ligand system 35 binds dopamine derivative 37 and phloroglucinol (1,3,5trihydroxybenzene) with association constants of Ka = 60 and 3500 M - t, respectively. The affinity of the Cu(I) analogon of 36 for 37 was very similar to that of 36 itself and amounted to K, = 60 M - 2.