Effect of a single chalcogen atom variation on the chalcogen bond parameters: CSD analysis and theoretical calculations

Abstract

Like other factors (internal – substituents and nucleophile; external – coordination, cooperation, solvent polarity, etc.), the chalcogen atom Ch (O, S, Se or Te) replacement at element–Ch⋯nucleophile chemical leitmotifs can also be used as a powerful strategy in the regulation of chalcogen bond parameters (strength and directionality). In this work, we analyze the effect of chalcogen atoms on the strength and directionality of chalcogen bonding (ChB) in various classes of organic compounds taken from the Cambridge Structural Database (CSD). Based on the experimental data (from CSD) and theoretical calculations, we conclude that the expected trend (O ≪ S < Se < Te) for enhancing strength and directionality of ChB does not always occur due to weak characters of Ch⋯nucleophile interactions.