Three L-Tryptophan based chiral Schiff bases namely, 2-((5-chloro-2-hydroxybenzylidene)amino)-3-(1H-indol-3-yl)propanoic acid (i), 2-((5-bromo-2-hydroxybenzylidene)amino)-3-(1H-indol-3-yl) propanoic acid (ii) and 2-((2-hydroxy-5-iodobenzylidene)amino)-3-(1H-indol-3-yl)propanoic acid (iii) were synthesized and their corrosion inhibition behaviour on corrosion of carbon steel in 1 M hydrochloric acid (HCl) solution was investigated by means of weight loss and electrochemical techniques. The inhibitory action of Schiff bases was found to be mixed-type, it’s adsorption on carbon steel surface obeys the Langmuir adsorption isotherm and involves both physisorption and chemisorption mechanisms. Quantum chemical calculations predicted an inhibition order of iii > ii > i, is in good agreement with the experimental order. The impact of halide substitution on Schiff bases towards its anti-corrosion ability was explored.