Comparison of Bifurcated Halogen with Hydrogen Bonds

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Jan 15

PMID 33445461

Citations 5

Authors

Steve Scheiner

Affiliations

Soon will be listed here.

Abstract

Bifurcated halogen bonds are constructed with FBr and FI as Lewis acids, paired with NH and NCH bases. The first type considered places two bases together with a single acid, while the reverse case of two acids sharing a single base constitutes the second type. These bifurcated systems are compared with the analogous H-bonds wherein FH serves as the acid. In most cases, a bifurcated system is energetically inferior to a single linear bond. There is a larger energetic cost to forcing the single σ-hole of an acid to interact with a pair of bases, than the other way around where two acids engage with the lone pair of a single base. In comparison to FBr and FI, the H-bonding FH acid is better able to participate in a bifurcated sharing with two bases. This behavior is traced to the properties of the monomers, in particular the specific shape of the molecular electrostatic potential, the anisotropy of the orbitals of the acid and base that interact directly with one another, and the angular extent of the total electron density of the two molecules.

Citing Articles

Crystal Structure Survey and Theoretical Analysis of Bifurcated Halogen Bonds.

Michalczyk M, Zierkiewicz W, Scheiner S Cryst Growth Des. 2022; 22(11):6521-6530.

PMID: 36345386 PMC: 9634799. DOI: 10.1021/acs.cgd.2c00726.

Anticooperativity of Multiple Halogen Bonds and Its Effect on Stoichiometry of Cocrystals of Perfluorinated Iodobenzenes.

Bedekovic N, Pitesa T, Erakovic M, Stilinovic V, Cincic D Cryst Growth Des. 2022; 22(4):2644-2653.

PMID: 35401054 PMC: 8991082. DOI: 10.1021/acs.cgd.2c00077.

Ability of Lewis Acids with Shallow σ-Holes to Engage in Chalcogen Bonds in Different Environments.

Wysokinski R, Zierkiewicz W, Michalczyk M, Scheiner S Molecules. 2021; 26(21).

PMID: 34770803 PMC: 8586936. DOI: 10.3390/molecules26216394.

Hydrogen Bonding in Natural and Unnatural Base Pairs-A Local Vibrational Mode Study.

Beiranvand N, Freindorf M, Kraka E Molecules. 2021; 26(8).

PMID: 33919989 PMC: 8071019. DOI: 10.3390/molecules26082268.

Anion-Anion Interactions in Aerogen-Bonded Complexes. Influence of Solvent Environment.

Grabarz A, Michalczyk M, Zierkiewicz W, Scheiner S Molecules. 2021; 26(8).

PMID: 33917030 PMC: 8067769. DOI: 10.3390/molecules26082116.

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