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Chiral Softballs:  Synthesis and Molecular Recognition Properties

AuthorsRivera, José M.; Martín, Tomás ; Rebek, Julius Jr.
Noncovalent interactions
Issue Date10-May-2001
PublisherAmerican Chemical Society
CitationJournal of the American Chemical Society 123(22): 5213–5220
AbstractStudies on the different congeners of the softball were undertaken to explore structural variants for enantioselective encapsulation. Two different spacer elements in the monomeric subunit render the dimeric softball chiral although the monomer itself is achiral. The dimers represent capsules with dissymmetric cavities with volumes ranging from 190 to 390 Å3. The cavities are distorted spheres, and asymmetric guests, such as naturally occurring terpenes, generally prefer one enantiomer of the capsule to its mirror image. The selectivities are moderate (up to 4:1). The complexation studies show that the host capsules are flexible enough to arrange themselves comfortably around a guest but still maintain enough rigidity to be influenced by the occupancy of a chiral guest. The enantiomeric capsules can interconvert (racemize) by dissociation and recombination of their subunits.
Publisher version (URL)https://doi.org/10.1021/ja004080i
Appears in Collections:(IPNA) Artículos
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