A series of norephedrine-based Schiff bases (1a-6a and 1b-6b) were synthesized by reacting substituted salicylaldehydes with d-norephedrine or l-norephedrine. The structure of these compounds was confirmed by elemental analyses and spectroscopic techniques. The molecular structures of 5a and 6a have been determined by X-ray crystallography, which revealed that the compounds are in the oxoamino form, with bent intramolecular N-H···O (N···O≈2.58Å) hydrogen bonds and that they are associated in dimers bridged by linear intermolecular O-H···O (O···O≈2.69Å) hydrogen bonds. The density functional theory calculations on 5a confirmed that the oxoamino form is more stable than the phenolimino form by 12.2kcal/mol. All the compounds were evaluated for their antibacterial activity using resazurin dye as indicator by twofold dilution method against four bacteria namely, Bacillus subtilis (NCIM2718), Staphylococcus aureus (NCIM5021), Escherichia coli (NCIM2931), and Proteus vulgaris (NCIM2813). © 2011 John Wiley & Sons A/S.