Graphical Abstract Abstract Halogen bonds (XBs) are non-covalent R-X···B interactions where heavy halogens (X = Cl, Br, I) act as electrophilic species interacting with Lewis bases (B). This highly directional type of interaction is mostly explained by the existence of a positive region on the molecular electrostatic potential located at the tip of the halogen (called σ-hole), arising from polarization of the R-X covalent bond. Following the recognition of the significance of XBs in

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... structures [1], their application in rational drug design, amongst other areas, has been increasingly explored. In this context, the development of computational tools accurately modelling XB is of paramount importance. This is particularly challenging in the case of force field (FF)-based methods, where XBs are typically modelled by introducing a positive extra-point (EP) of charge to mimic the σ-hole [2]. Though different schemes for EP parameterization have been