Ralf Haiges - Conformational study via 19F NMR spectroscopy: Emergence of trifluoromethyl label as a conformational stabilizer and a probe.

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      Publication Details (including relevant citation   information): Prakash, G. K. Surya, Wang, Fang, Ni,   Chuanfa, Shen, Jingguo, Yudin, Andrei K., Haiges, Ralf, Mathew,   Thomas, Olah, George A., 20th Winter Fluorine Conference,   American Chemical Society, Division of Fluorine Chemistry, St.   Pete Beach, FL, United States, January 9-14,   2011, pp FLUO-89

      Abstract: Conformational isomerism plays a   significant role in chem. transformations, asym. catalysis and   mol. recognition. Conformational anal. of nonrigid mols. is of   fundamental interest in org. chem. Although extensively applied,   the conventional NMR techniques, such as dynamic nuclear magnetic   spectroscopy (DNMR) and nuclear Overhauser enhancement   spectroscopy (nOe), are extremely time-consuming and tedious for   the conformational analyses of complex systems under various   conditions. As a consequence, the systemic studies of the   conformational environment-dependence of complex org. mols. are   rather rare. We have developed a unique strategy by introducing   the trifluoromethyl (CF3-) moiety as a conformational stabilizer   and a probe to a no. of cinchona alkaloids. Based on such   bifunctionality of the CF3 moiety, the response of individual   conformers to a series of environmental parameters can be   feasibly investigated to provide an immediate insight into the   conformational behavior of org. mols. via 19F NMR spectroscopy.   [on SciFinder(R)]

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