NeighboringChalcogen Bonding for Controlling DynamicImine Chemistry in Aqueous Media

The impact of varied chalcogen bonds (sulfur, selenium, tellurium, and telluronium) on dynamic imine chemistry in aqueous solution is presented by introducing a carboxylate group or cationic telluronium into arylaldehydes. The role of chalcogen bonding in regulating the kinetics and thermodynamics of imine formation/exchange was elucidated through experimental and computational evidence, affording the largest effect for tellurium/telluronium compounds. By leveraging multivalent chalcogen bonding, telluronium-containing aldehyde enabled labeling of the <i>N</i>-terminus of amino acids in neutral buffer.