Salicylaldehyde　derivatives　and　their　imines　are　important　building　blocks　in　organic　and　supramolecular　chemistry.　In　an　effort　to　expand　structural　diversity　in　the　current　work　we　changed　ortho-OH　in　salicylaldehyde　to　NH　of　amide/sulfonamide　and　investigated　the　effect　of　resulting　intramolecular　hydrogen　bonds　on　imine　dynamic　covalent　chemistry　(DCC).　A　suite　of　ortho-aminobenzaldehydes　were　readily　synthesized,　and　X-ray　and　NMR　data　validated　the　existence　of　NH⋯O　intramolecular　hydrogen　bonds.　The　formation　and　exchange　of　imines　were　then　studied　in　acetonitrile,　and　the　acidity　of　OH/NH　significantly　influenced　the　thermodynamics　and　kinetics　of　imine　reactions.　Furthermore,　the　role　of　OH/NH⋯N　hydrogen　bonds　on　imines　was　elucidated　by　the　shift　of　aldehyde　exchange　equilibrium.　Finally,　the　formation　of　imines　was　achieved　in　aqueous　solutions.　The　mechanistic　insights　could　pave　the　way　for　future　applications　in　assembly　and　labelling.　©　2020　Elsevier　Ltd