The design of anion–π interactions and hydrogen bonds for the recognition of chloride, bromide and nitrate anions

Literature Information

Publication Date 2021-04-21
DOI 10.1039/D1CP00113B
Impact Factor 3.676
Authors

Renato Pereira Orenha, Vanessa Borges da Silva, Giovanni Finoto Caramori, Maurício Jeomar Piotrowski, Glaucio Regis Nagurniak, Renato Luis Tame Parreira


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Abstract

The role of anions in several biochemical processes has given rise to enormous interest in the identification/exploration of compounds with the potential ability to recognize anions. Here, an anthracene–squaramide conjugated compound, O2C4[NH(C14H10)][(NH(C6H6)], has been modified through the substitutions (i) H → F and (ii) H → OH at the anthracene and benzene rings to improve the capabilities of these structures for recognizing chloride, bromide, and nitrate anions. Through an energy decomposition analysis method, the recognition of the anions is chiefly identified as a non-covalent process. H → F substitutions at the benzene ring and, principally, the anthracene ring favor anion recognition, since H → F substitutions create a π-acid region in the aromatic ring, as indicated based on the molecular electrostatic potential surfaces. Similarly, H → OH substitutions also improve the recognition of anions, which is related to the establishment of partly covalent chemical bonds of the form O–H⋯(Cl−, Br− and O−), which are verified based on the quantitative analysis of the maximum and minimum values of the molecular electrostatic potential surfaces and the quantum theory of atoms in molecules method. The presence of large electron density has a key role in the recognition of Cl− anions, and the more favorable electrostatic interactions between the anthracene structure and Br− anions, relative to NO3− anions, mean that receptor⋯Br− interactions are more attractive than receptor⋯NO3− ones. These data can contribute to the design of structures with the relevant abilities to interact with anions.

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Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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