Hammett Structural Relationships Revealed in Chalcogen-Bonded Co-Crystals of Electron-Rich Pyridines with 4′-Substituted Ebselen Derivatives

Abstract

In this work, a detailed Hammett structure-structure correlation was applied to a range of chalcogen-bonded co-crystals prepared by combining 4′-substituted derivatives of the selenium-based drug ebselen with three different 4-amino-substituted pyridine-based chalcogen bond acceptors of differing basicities. This established that the N···Se chalcogen bond distance is well within the sum of the van der Waals radii of Se and N and is sensitive to the electronic nature of the substituent. Thus, N···Se distances ranging from 2.2424(5) to 2.4496(9) Å were observed, with the shorter distances being observed in co-crystals of ebselen substituted with electron-withdrawing groups. Associated with tre..