Carbon-iodine atropisomerism on triazole and triazolium frameworks: a breathing axle with divergent adaptivity.

ABSTRACT: Atropisomerism around a carbon-iodine(iii) bond represents a rare form of chirality centered on a long, polarizable hypervalent linkage. Embedding this C-I(iii) bond into an inherently asymmetric, diadamantylated triazole scaffold creates a vivid platform that reveals how such a bond responds to steric and electronic perturbations. Neutral triazole- and cationic triazolium-benziodoxoles display similarly high atropostability (racemization half-lives of several years at 25 °C), arising from opposing effects introduced by N-methylation: electronic weakening of the C-I bond versus steric buttressing that restricts rotation. Under acidic conditions, however, their behaviors diverge; the triazole derivative undergoes accelerated rotation, whereas the triazolium analogue retains su

SUBMITTER: Nambu R 

PROVIDER: S-EPMC12863260 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature