A water soluble pyridine containing a Schiff base as chemosensor was designed and then synthesised. The chemosensor (L) was synthesized by reacting pyridoxal and 2-aminoethanol and then comprehensively characterized using elemental analysis, spectroscopic methods (infrared, ultraviolet-visible, nuclear magnetic resonance ( 1 H-NMR and 13 C-NMR) spectroscopy), electrospray ionization mass spectroscopy, and single crystal X-ray crystallography. The designed compound showed excellent specificity and sensitivity (detection limit ¼ 4.18 Â 10 À6 M) towards Ag + ions in preference to other interfering cations (Ca 2+ , Co 2+ , Cu 2+ , Fe 2+ , Fe 3+ , Hg 2+ , VO 2+ , K + , Li + , Mn 2+ , Na + , Ni 2+ , Pb 2+ and Zn 2+ ) in aqueous solution.The (L) showed a selective chromogenic behavior towards Ag + ions by changing the color of the solution from light yellow to red, a change which can be detected with the naked eye. A simple and cost effective test kit was prepared for the detection of silver ion in water samples. Time-dependent density functional theory calculations were carried out to help understand the sensing mechanism.