Acid-Base and Anion Binding Properties of Tetrafluorinated 1,3-Benzodiazole, 1,2,3-Benzotriazole and 2,1,3-Benzoselenadiazole

Acid-Base and Anion Binding Properties of Tetrafluorinated 1,3-Benzodiazole, 1,2,3-Benzotriazole and 2,1,3-Benzoselenadiazole Full article

Journal

ChemPhysChem
ISSN: 1439-4235 , E-ISSN: 1439-7641

Output data

Year: 2021, Volume: 22, Number: 22, Pages: 2329-2335 Pages count : 7 DOI: 10.1002/cphc.202100475

Tags

acid-base properties; anion binding; aza-heterocycles; hole interactions; organofluorine compounds

Authors

Parman Elisabeth ¹ , Lõkov Märt ¹ , Järviste Robert ¹ , Tshepelevitsh Sofja ¹ , Semenov Nikolay A. ² , Chulanova Elena A. ² , Salnikov Gejrgy E. ² , Prima Datya O. ^2,4 , Slizhov Yuri G. ³ , Leito Ivo ¹ , Zibarev Andrey V. ²

Affiliations

1	Institute of Chemistry, University of Tartu, Ravila 14a, Tartu, 50411, Estonia
2	Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9 Lavrentiev Avenue, Novosibirsk, 630090, Russian Federation
3	Department of Chemistry, National Research University – Tomsk State University, 36 Lenin Avenue, Tomsk, 634050, Russian Federation
4	Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Avenue, Moscow, 119991, Russian Federation

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. © 2021 Wiley-VCH GmbH

Parman E. , Lõkov M. , Järviste R. , Tshepelevitsh S. , Semenov N.A. , Chulanova E.A. , Salnikov G.E. , Prima D.O. , Slizhov Y.G. , Leito I. , Zibarev A.V.
Acid-Base and Anion Binding Properties of Tetrafluorinated 1,3-Benzodiazole, 1,2,3-Benzotriazole and 2,1,3-Benzoselenadiazole
ChemPhysChem. 2021. V.22. N22. P.2329-2335. DOI: 10.1002/cphc.202100475 WOS Scopus

Web of science	WOS:000703570600001
Scopus	2-s2.0-85116384394
OpenAlex	W3195006497