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N-heterocyclic carbene (NHC) adducts have shown remarkable biological potential for numerous medical applications. With an aim to improve biological potential of benzimidazolium salts, newer analogues of benzimidazole and their silver complexes were synthesized and characterized. Synthesized salts (L 1 -L 2) and silver complexes (C 1 -C 2) were confirmed through elemental analysis, UV–visible spectroscopy, FTIR, 1H NMR &13C NMR spectroscopy. The compounds C1 & C2 were found stable in solution form for studied time period when examined spectroscopically and showed optimum lipophilicity when measured for their partition coefficient through flask shake method. Synthesized compounds showed good antimicrobial potential against gram positive bacterial strain S. Aureus with IC 50 2.02±0.12 and 2.11±0.13 µM respectively while 2.11±0.1 and 2.28±0.17 µM against gram negative bacterial strain E. Coli for C1 and C2 respectively. The interaction study of the related compounds with DNA was predicted by molecular docking study, which confirmed that the studied compound C1 (-8.04 kcal/mol) has a higher binding energy than compound C2 (-4.23 kcal/mol); Also, the compound C1 exhibits a better affinity against to DNA than Ethidium bromide (-7.68 kcal/mol) and cisplatin (-6.21 kcal/mol).The claim was practically assured through spectroscopic and viscometeric method which confirmed that compounds have good affinity for DNA with binding constant kb, 5.78×104 M-1 and 6.84×104 M-1 for C1 and C2 respectively. [Display omitted] • Four new compounds, NHC binuclear salts and silver complexes were synthesized. • Compounds were confirmed through spectroscopy and elemental analysis. • In Vitro assay confirmed the dose dependent antimicrobial and antioxidant potential of studied compounds. • In-vitro and In-silico study confirmed that DNA could be potential target for the studied compounds for their activity. [ABSTRACT FROM AUTHOR]