Absolute configuration of conformationally flexible cis-dihydrodiol metabolites by the method of confrontation of experimental and calculated electronic CD spectra and optical rotations |
| |
Authors: | Kwit Marcin Sharma Narain D Boyd Derek R Gawronski Jacek |
| |
Affiliation: | Department of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland. |
| |
Abstract: | We have determined the absolute configurations of conformationally flexible cis-dihydrodiol metabolites (cis-1,2-dihydroxy-3,5-cyclohexadienes), bearing different substituents (e.g., Br, F, CF3, CN, Me) in 3- and 5-positions, by the method of confrontation of experimental and calculated electronic CD spectra and optical rotations. Convergent results were obtained by both methods in eight out of ten cases. For the difficult cases, where either conformer population and/or chiroptical properties (calculated rotational strengths of the long-wavelength Cotton effect or optical rotations) of contributing conformers remain inconclusive, the absolute configuration could still be correctly assigned based on one of the biased properties (either ECD or optical rotation). This approach appears well-suited for a broad spectrum of conformationally flexible chiral molecules. |
| |
Keywords: | absolute configuration circular dichroism conformation analysis density functional calculations optical rotation |
本文献已被 PubMed 等数据库收录! |
|