Unifying and Self-Aggregation of Enantiopure and Racemic Molecular Tweezers Based on the Bicyclo[3.3.1]nonane Framework <<>>
Written by Carl-Johan Wallentin, Torbjörn Wixe, Ola F. Wendt, Karl-Erik Bergquist, Kenneth Wärnmark on February 24, 2010 – 12:16 pm -A span of molecular tweezers (syn-4) that consists of quinoline and pyrazine units fused to a bicyclic framework is presented. The tweezers were synthesised both as a racemic hodgepodge (rac-4) and an enantiomerically conceptual figure ((R,R,R,R)-4) starting from either racemic or enantiomerically spotless bicyclo[3.3.1]nonane-2,6-dione (3). Homochiral dimers were observed in the solid delineate for rac-4. The self-association of both rac-4 and (R,R,R,R)-4 was feigned in liquid. A soft-headed self-association non-stop in CDCl3 was estimated by 1H NMR spectroscopic dilution titration experiments in both cases, following not too proton resonances. For this purpose, a ordinary normalisation sport imitate for the spot on target constancy of association constants from multiple datasets was developed. In set to the steadfast state, no diastereomeric discernment was observed for rac-4 in mixture <<>>
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