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Exploring the Capability of Mechanically Interlocked Molecules in Anion Recognition: A Computational Insight

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide The present study elucidated the role of both hydrogen and halogen bonds, from an electronic structure perspective, in the anion recognition process by the [2]catenane ( 1 ) containing a moiety with hydrogen bond donors entangled with another macrocyclic halogen bond donor. Spherical and nonspherical anions have been employed. The roles of different σ–hole donors have also been considered. The structure of 1 was modified by incorporating other σ–hole donors, namely bromine, chlorine, fluorine, as well as −Te–CH 3 as a chalcogen bond donor, leading to the modified [2]catenanes 2 – 5 . Insights into anion recognition were gained by quantifying the contributions of not only the mechanical but also hydrogen and halogen/chalcogen bonds to anion recognition using the GKS-EDA energy partition scheme and homodesmostic reactions scheme. GKS-EDA reveals that the anions Cl – and TS – exhibit the most stabilizing interactions with the 1 binding pocket. The EDA results confirm that by changing from a stronger σ-hole donor (I) to a weaker σ-hole donor (F) will have a considerable impact on anion interaction, thereby demonstrating that the halogen bonds formed between the [2]catenane and the anion play a pivotal role.

Source: ACS Physical Chemistry Au

DOI: 10.1021/acsphyschemau.4c00089

Authors: Fábio J. Amorim, Giovanni F. Caramori

Institution: Universidade Federal de Santa Catarina

Language: English

Topic: Supramolecular Chemistry and Complexes

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,500

Funders: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico, Universidade Federal de Santa Catarina