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　N-terminus　of　amino　acids　in　neutral　buffer.