Substituent Effects on Sulfur Phenolate Exchange Reactions: Reactivity and Bonding Analysis.

ABSTRACT: The Sulfur Phenolate Exchange reaction (SuPhenEx) provides a fluorine-free alternative S(VI) exchange chemistry by substituting nitrophenolate as the leaving group instead of fluoride (as in SuFEx reactions), offering a synthetically appealing and environmentally friendly approach in click chemistry. Despite its significance, the reaction mechanism and the underlying electronic interactions in the course of the reaction have yet to be thoroughly explored at the molecular level. Here, we elucidate the electronic interactions of a series of SuPhenEx model reactions between various para-substituted phenolates (p-R-Ph-O^-) as nucleophiles and PhSO₂-OPh-p-NO₂ as an electrophile, in both gas and solvent (acetonitrile) phases. As tools, we apply the Activation Stra

SUBMITTER: Krishna A 

PROVIDER: S-EPMC12598377 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature