For developing antiwear additives with high efficiency but with low SAPS, N-substituted quinolinium halides, [DIP-Q] + Br -[DIP-Q=1-(3-(1,3-dioxoisoindolin-2-yl)propyl)quinolon-1-ium], [DIE-Q] + Br -[DIE-Q=1-(3-(1,3-dioxoisoindolin-2-yl)ethyl)quinolon-1-ium], [P-Q] + I -[P-Q=propylquinolon-1-ium] and [M-Q] + I -[M-Q=methylquinolon-1-ium] have been prepared and characterized by 1 H and 13 C NMR spectroscopic techniques. Tribological performance of these quinoline based quaternary salts as antiwear additives in paraffin oil has been assessed on four-ball test rig. The observed results have been compared with those of zinc dibutyldithiophosphate (ZDDP), a high SAPS additive. The tribo-testing of these additives has been performed using 1% w/v additives concentration at different loads and time. Potentiality of these compounds as antiwear additives is evident from their observed tribological data; mean wear scar diameter (MWD), friction coefficient (µ), mean wear volume (MWV) and wear rates. All the quinolinium derivatives prove to be better antiwear additives than ZDDP. Among the tested synthesized compounds, [DIP-Q] + Br -exhibits the best tribological behavior followed by [DIE-Q] + Br -, [P-Q] + I -and then [M-Q] + I -. The surface topography of worn surface studied by Scanning Electron Microscopy (SEM) and Atomic Force Microscopy (AFM) shows that surface roughness is reduced to a greater extent in case of quinolinium derivatives than that lubricated with ZDDP or base oil alone. Energy Dispersive X-Ray (EDX) and X-ray Photoelectron Spectroscopy (XPS) analysis of worn surfaces in presence of quinolinium additives shows that tribofilm is composed of FeBr 3 , Fe 3 O 4 and organic compounds containing carbonyl and imine bonds. Theoretical investigations using quantum chemical calculations are indicative of significant chemical interactions of these quinolinium additives with metal surface which are strongly supported by the observed experimental data.