Absolute configuration of conformationally flexible cis-dihydrodiol metabolites by the method of confrontation of experimental and calculated electronic CD spectra and optical rotations

M. Kwit, Narain Sharma, Derek Boyd, J. Gawronski

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)5812-5821
Number of pages10
JournalChemistry-a European Journal
Volume13 (20)
Issue number20
DOIs
Publication statusPublished - Apr 2007

ASJC Scopus subject areas

  • Chemistry(all)

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