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

Autor(es)

Orenha, Renato Pereira ^[1] ; da Silva, Vanessa Borges ^[1] ; Caramori, Giovanni Finoto ^[2] ; Piotrowski, Mauricio Jeomar ^[3] ; Nagurniak, Glaucio Regis ^[4] ; Parreira, Renato Luis Tame ^[1]

Afiliação do(s) autor(es)

^[1] Univ Franca, Nucleo Pesquisas Ciencias Exatas & Tecnol, Franca, SP - Brazil

^[2] Univ Fed Santa Catarina, Dept Quim, Campus Univ Trindade, CP 476, BR-88040900 Florianopolis, SC - Brazil

^[3] Univ Fed Pelotas, Dept Phys, POB 354, BR-96010900 Pelotas, RS - Brazil

^[4] Univ Fed Santa Catarina, Dept Exact Sci & Educ, BR-89036004 Blumenau, SC - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Physical Chemistry Chemical Physics; v. 23, n. 19, p. 11455-11465, MAY 21 2021.
• Citações Web of Science: 0

Resumo

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 pi-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-HMIDLINE HORIZONTAL ELLIPSIS(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 receptorMIDLINE HORIZONTAL ELLIPSISBr- interactions are more attractive than receptorMIDLINE HORIZONTAL ELLIPSISNO3- ones. These data can contribute to the design of structures with the relevant abilities to interact with anions. (AU)

• Processo FAPESP: 11/07623-8 - Utilização de métodos mecânicos-quânticos para estudo das ligações e interações químicas em sistemas auto-organizados com aplicação em catálise, química medicinal, eletrocromismo, armazenamento e conversão de energia
• Beneficiário: Renato Luis Tame Parreira
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores
• Processo FAPESP: 19/19175-1 - 5a Escola de Química Computacional - "Modelagem em Química Supramolecular"
• Beneficiário: Renato Luis Tame Parreira
• Modalidade de apoio: Auxílio Organização - Reunião Científica
• Processo FAPESP: 17/24856-2 - O Mecanismo da Reação de Substituição do Ligante Nitrosil por Aqua em Compostos de Coordenação de Rutênio
• Beneficiário: Renato Pereira Orenha
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado