Going beyond structural effects: explicit solvation influence on the rotational isomerism of C-glycosylated flavonoids

Abstract

C-glycosyl-flavonoids are phytochemical natural products that possess different biological applications. Several compounds from this class exhibit rotational isomerism, evidenced by NMR signal duplication. This phenomenon is usually associated with the...

Sequential nucleophilic aromatic substitutions on cyanuric chloride: synthesis of BODIPY derivatives and mechanistic insights

“…The spectroscopic profile led us to hypothesize the occurrence of rotational isomerism, which can manifest in a set of conformers with restricted bond rotation along a single bond, as observed in our previous studies. 34,35 The restriction creates a high interconversion barrier (Δ G ‡ > 20 kcal mol −1 ) between two conformers allowing for the identification of the rotamers in the NMR spectra. To corroborate this hypothesis, we investigated the behavior of the aldehyde proton H j of compound 3 in the 1 H-NMR spectrum with increasing temperature.…”