Acid-Base and Anion Binding Properties of Tetrafluorinated 1,3-Benzodiazole, 1,2,3-Benzotriazole and 2,1,3-Benzoselenadiazole |
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| Authors: | Elisabeth Parman Dr Märt Lõkov Robert Järviste Dr Sofja Tshepelevitsh Dr Nikolay A Semenov Dr Elena A Chulanova Dr Georgy E Salnikov Dr Darya O Prima Dr Yuri G Slizhov Prof Dr Ivo Leito Prof Dr Andrey V Zibarev |
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| Institution: | 1. Institute of Chemistry, University of Tartu, Ravila 14a, 50411 Tartu, Estonia;2. Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9 Lavrentiev Avenue, 630090 Novosibirsk, Russia;3. Department of Chemistry, National Research University – Tomsk State University, 36 Lenin Avenue, 634050 Tomsk, Russia |
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| 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 the Brønsted acidity of the diazole and triazole scaffolds and the Lewis acidity of selenadiazole scaffold decreases the 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 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 a reasonable metric for design and synthesis of new anion receptors with selenadiazole-diazole/triazole hybrids as a special target. Related chlorinated compounds are also discussed. |
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| Keywords: | acid-base properties anion binding aza-heterocycles hole interactions organofluorine compounds |
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