Conformational behavior of cinchonidine revisited: a combined theoretical and experimental study.
Conformational space of cinchonidine has been explored by means of ab initio potential and free energy surfaces, and the temperature-induced changes of conformational populations were studied by a combined NOESY-DFT analysis. The DFT-derived potential energy surface investigation identified four new conformers. Among them, Closed(7) is substantially relevant to fully understand the conformational behavior. The energy surfaces gave access to the favored transformation pathways at different temperatures (280-320 K). They also revealed the reasons for the negligible presence of energetically stable conformers and explained the experimentally observed temperature dependence of the populations.
Urakawa
Atsushi
A
Institute for Chemical and Bioengineering, Department of Chemistry and Applied Biosciences, ETH Zurich, Hönggerberg, HCI, 8093 Zurich, Switzerland.
Meier
Daniel M
DM
Rüegger
Heinz
H
Baiker
Alfons
A
D002930:Cinchona Alkaloids / Q000737:chemistry*; D008968:Molecular Conformation; D011789:Quantum Theory; D013499:Surface Properties; D013696:Temperature; D013816:Thermodynamics
D002930:Cinchona Alkaloids; C041622:cinchonidine