Elisabeth Parman, Märt Lõkov, Robert Järviste
Aug 16, 2021
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Chemphyschem : a European journal of chemical physics and physical chemistry
Abstract
The influence of fluorination on the acid-base properties and the capacity of structurally related 6-5 bicyclic compounds - 1,3-benzodiazole 1, 1,2,3-benzotriazole 2 and 2,1,3-benzoselenadiazole 3 to σ-hole interactions, i.e. hydrogen (1 and 2) and chalcogen (3) bondings, is studied experimentally and computationally. The tetrafluorination increases Brønsted acidity of diazole and triazole scaffolds and Lewis acidity of selenadiazole scaffold and decreases basicity. Increased Brønsted acidity facilitates anion binding via the formation of hydrogen bonds; particularly, tetrafluorinated derivative of 1 (compound 4) binds Cl-. Increased Lewis acidity of tetrafluorinated derivative of 3 (compound 10), however, is not enough for binding with Cl- and F- via the formation of chalcogen bonds in contrast to previously studied Te analog of 10. It is suggested that the maximum positive values of molecular electrostatic potential at the σ-holes, VS,max, can be reasonable metrics in the further design and synthesis of new anion receptors, with selenadiazole-diazole / triazole hybrids as a special target. Related chlorinated compounds are also discussed.