Halogen Bonds, Chalcogen Bonds, Pnictogen Bonds, Tetrel Bonds and Other σ-hole Interactions: a Snapshot of Current Progress

Overview

Journal Acta Crystallogr C Struct Chem

Specialty Chemistry

Date 2023 May 22

PMID 37212787

Authors

Lee Brammer

Anssi Peuronen

Thomas M Roseveare

Affiliations

Soon will be listed here.

Abstract

We report here on the status of research on halogen bonds and other σ-hole interactions involving p-block elements in Lewis acidic roles, such as chalcogen bonds, pnictogen bonds and tetrel bonds. A brief overview of the available literature in this area is provided via a survey of the many review articles that address this field. Our focus has been to collect together most review articles published since 2013 to provide an easy entry into the extensive literature in this area. A snapshot of current research in the area is provided by an introduction to the virtual special issue compiled in this journal, comprising 11 articles and entitled `Halogen, chalcogen, pnictogen and tetrel bonds: structural chemistry and beyond.'

Citing Articles

The nature of halogen bonding: insights from interacting quantum atoms and source function studies.

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Anion transporters based on halogen, chalcogen, and pnictogen bonds: towards biological applications.

Singh A, Torres-Huerta A, Meyer F, Valkenier H Chem Sci. 2024; .

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Key-to-lock halogen bond-based tetragonal pyramidal association of iodonium cations with the lacune rims of beta-octamolybdate.

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Evaluation of Concomitant Halogen and Pnictogen Bonds in Cocrystals of Imines Derived from 2-Nitrobenzaldehyde and 4-Haloaniline.

Baus Topic N, Bedekovic N, Poljanic L, Stilinovic V, Cincic D Cryst Growth Des. 2024; 24(7):3010-3020.

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References

Zhao Y, Cotelle Y, Sakai N, Matile S . Unorthodox Interactions at Work. J Am Chem Soc. 2016; 138(13):4270-7. DOI: 10.1021/jacs.5b13006. View

Lorpaiboon W, Bovonsombat P . Halogen bond-induced electrophilic aromatic halogenations. Org Biomol Chem. 2021; 19(35):7518-7534. DOI: 10.1039/d1ob00936b. View

Kampes R, Zechel S, Hager M, Schubert U . Halogen bonding in polymer science: towards new smart materials. Chem Sci. 2021; 12(27):9275-9286. PMC: 8278954. DOI: 10.1039/d1sc02608a. View

Hein R, Beer P . Halogen bonding and chalcogen bonding mediated sensing. Chem Sci. 2022; 13(24):7098-7125. PMC: 9214886. DOI: 10.1039/d2sc01800d. View

Politzer P, Murray J, Clark T . σ-Hole bonding: a physical interpretation. Top Curr Chem. 2014; 358:19-42. DOI: 10.1007/128_2014_568. View

Daolio A, Pizzi A, Calabrese M, Terraneo G, Bordignon S, Frontera A . Molecular Electrostatic Potential and Noncovalent Interactions in Derivatives of Group 8 Elements. Angew Chem Int Ed Engl. 2021; 60(38):20723-20727. PMC: 8519081. DOI: 10.1002/anie.202107978. View

Bauza A, Frontera A . Aerogen Bonding Interaction: A New Supramolecular Force?. Angew Chem Int Ed Engl. 2015; 54(25):7340-3. DOI: 10.1002/anie.201502571. View

Ivanov D, Bokach N, Kukushkin V, Frontera A . Metal Centers as Nucleophiles: Oxymoron of Halogen Bond-Involving Crystal Engineering. Chemistry. 2021; 28(2):e202103173. PMC: 9298210. DOI: 10.1002/chem.202103173. View

Selvakumar K, Singh H . Adaptive responses of sterically confined intramolecular chalcogen bonds. Chem Sci. 2018; 9(35):7027-7042. PMC: 6137456. DOI: 10.1039/c8sc01943f. View

10.

Peluso P, Mamane V . Stereoselective Processes Based on σ-Hole Interactions. Molecules. 2022; 27(14). PMC: 9323542. DOI: 10.3390/molecules27144625. View

11.

Persch E, Dumele O, Diederich F . Molecular recognition in chemical and biological systems. Angew Chem Int Ed Engl. 2015; 54(11):3290-327. DOI: 10.1002/anie.201408487. View

12.

Varadwaj P, Varadwaj A, Marques H, Yamashita K . Chalcogen Bonding in the Molecular Dimers of WCh (Ch = S, Se, Te): On the Basic Understanding of the Local Interfacial and Interlayer Bonding Environment in 2D Layered Tungsten Dichalcogenides. Int J Mol Sci. 2022; 23(3). PMC: 8835845. DOI: 10.3390/ijms23031263. View

13.

Vargas Jentzsch A, Hennig A, Mareda J, Matile S . Synthetic ion transporters that work with anion-π interactions, halogen bonds, and anion-macrodipole interactions. Acc Chem Res. 2013; 46(12):2791-800. DOI: 10.1021/ar400014r. View

14.

Ding X, Chang Y, Ou C, Lin J, Xie L, Huang W . Halogen bonding in the co-crystallization of potentially ditopic diiodotetrafluorobenzene: a powerful tool for constructing multicomponent supramolecular assemblies. Natl Sci Rev. 2021; 7(12):1906-1932. PMC: 8288552. DOI: 10.1093/nsr/nwaa170. View

15.

Xiao L, Fu H . Enhanced Room-Temperature Phosphorescence through Intermolecular Halogen/Hydrogen Bonding. Chemistry. 2018; 25(3):714-723. DOI: 10.1002/chem.201802819. View

16.

Bamberger J, Ostler F, Garcia Mancheno O . Frontiers in Halogen and Chalcogen-Bond Donor Organocatalysis. ChemCatChem. 2020; 11(21):5198-5211. PMC: 6919929. DOI: 10.1002/cctc.201901215. View

17.

Corradi , Meille , Messina , Metrangolo , Resnati . Halogen Bonding versus Hydrogen Bonding in Driving Self-Assembly Processes Perfluorocarbon-hydrocarbon self-assembly, part IX. This work was supported by MURST (Cofinanziamento '99) and EU (COST-D12-0012). We thank Dr. A. Lunghi and Dr. P. Cardillo.... Angew Chem Int Ed Engl. 2000; 39(10):1782-1786. DOI: 10.1002/(sici)1521-3773(20000515)39:10<1782::aid-anie1782>3.0.co;2-5. View

18.

Nag T, Ovens J, Bryce D . Se and Te solid-state NMR and X-ray diffraction structural study of chalcogen-bonded 3,4-dicyano-1,2,5-chalcogenodiazole cocrystals. Acta Crystallogr C Struct Chem. 2022; 78(Pt 10):517-523. DOI: 10.1107/S2053229622008518. View

19.

Legon . Prereactive Complexes of Dihalogens XY with Lewis Bases B in the Gas Phase: A Systematic Case for the Halogen Analogue B small middle dot small middle dot small middle dotXY of the Hydrogen Bond B small middle dot small middle dot small middle dotHX. Angew Chem Int Ed Engl. 1999; 38(18):2686-2714. DOI: 10.1002/(sici)1521-3773(19990917)38:18<2686::aid-anie2686>3.0.co;2-6. View

20.

Evans N, Beer P . Advances in anion supramolecular chemistry: from recognition to chemical applications. Angew Chem Int Ed Engl. 2014; 53(44):11716-54. DOI: 10.1002/anie.201309937. View