Tin has one of the largest number of organometallic derivatives that are available for different commercial applications. In organic synthesis, organotin compounds participate as a precursor/catalyst in several organic transformations, and therefore it becomes imperative to study the interaction of these compounds with other co-precursor. This study explores the interaction of ethyl tin (IV) chloride (C2H5SnCl3), an organotin compound, with pyridine derivative using density functional theory (DFT) calculations. Pyridine derivatives has been known for their multifaceted role as solvent, base, ligand, catalyst, functional group and molecular scaffold in several organic reactions. In particular, here, we have considered pyridine as a base/donor molecule. In this study, we have considered a total of 11 compounds with their ortho, meta, and para derivatives, enumerating 33 (11×3) interactions among donor and acceptor compounds. Among ortho-derivative donors, the interaction of o-Phenylacetatopyridine (o-PhAcPy) with C2H5SnCl3 acceptor is thermodynamically most favorable. Similarly, in the case of meta and para