Conformational analysis of an optically active BILIRUBIN DIMETHYL ESTER (cas 19792-68-8) and bis-N,N-dimethyl amide by circular dichroism, NMR and molecular dynamics

Add time:09/24/2019    Source:sciencedirect.com

The dimethyl ester and bis-N,N-dimethylamide of an optically active analog of bilirubin (ßS,ß′S-dimethylmesobilirubin-XIIIα) is stabilized in a ridge-tile conformation by intramolecular hydrogen bonding, as detected by 1H-NMR and CD spectroscopy. The ridge-tile shape is most evident in nonpolar solvents, where very strong exciton coupling CD is evident: e.g., in benzene, Δϵmax412 −199, Δϵmax372+87 for the dimethyl ester and Δϵmax421-165, Δϵmax384+46 for the bis-N,N-dimethylamide.

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