jo000473o_si_001.pdf (749.62 kB)
Stereoisomerism of Molecular Multipropellers. 1. Static Stereochemistry of Bis- and Tris-triaryl Systems
journal contribution
posted on 2001-02-06, 00:00 authored by Josep Sedó, Nora Ventosa, Ma Antònia Molins, Miquel Pons, Concepció Rovira, Jaume VecianaThe static stereoisomerism of bis- and tris-triaryl systems has been analyzed by a systematic
stereochemical analysis, and the resulting theoretical predictions have been experimentally
confirmed by using reversed-phase HPLC and ESR and 1H NMR spectroscopies with a family of
seven distinct polychlorinated aromatic multipropellers. To analyze the static stereochemistry of
these molecules, we have developed a specific procedure that uses a symmetry-adapted symbolic
notation, allowing the theoretical prediction of both the number and symmetry of the isomers of
the investigated molecules. Due to the steric hindrance introduced by the presence of bulky chlorine
substituents, (all) conformational isomers can be characterized experimentally by several independent techniques confirming the theoretical stereochemical predictions. The different propeller
moieties that constitute the molecule appear to be nearly independent of each other. Consequently,
most of the observed isomers show comparable populations in solution at room temperature.