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On the recognition of chloride, bromide and nitrate anions by anthracene-squaramide conjugated compounds: a computational perspective

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Pereira Orenha, Renato
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On the recognition of chloride, bromide and nitrate anions by anthracene-squaramide conjugated compounds: a computational perspective
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Author
  • Pereira Orenha, Renato;
  • Da Silva, Vanessa Borges;
  • Caramori, Giovanni Finoto;
  • De Souza Schneider, Felipe;
  • Piotrowski, Mauricio Jeomar;
  • Contreras-García, Julia;
  • Cárdenas, Carlos;
  • Briese Goncalves, Marina;
  • Mendizábal Emaldia, Fernando;
  • Parreira, Renato Luis Tame;
Abstract
Anion recognition is widely used in several biological fields. Squaramide derived compounds appear as potential structures to recognize anions. Here, the bond mechanisms between the chloride (Cl-), bromide (Br-) and nitrate (NO3-) anions and anthracene-squaramide conjugated compounds are elucidated considering the influence of the: (i) number, (ii) nature, and (iii) position of the substituents: trifluoromethyl (-CF3) and nitro (-NO2). Energy decomposition analysis (EDA) shows that the interactions between Cl-, Br- and NO3- and anthracene-squaramide have an attractive interaction energy supported predominantly by electrostatic energy followed by orbital contribution. Molecular electrostatic potential (MEP) surfaces imply electrostatic interactions between Cl-, Br- and the oxygen atom from NO3- and the hydrogen atoms from N-H and C-H bonds present in the squaramide structure, and an aryl group, respectively. Cl- interacts with the receptors more strongly than Br-. The NO3- recognition is less attractive than those presented by Cl- and Br-, in agreement with the hardness-softness features of these anions. Importantly, one and, mostly, two group substitutions, -H -> -CF3 or -NO2, favor the recognition of Cl-, Br- and NO3- due to the increase of the polarization in the receptor-NHMIDLINE HORIZONTAL ELLIPSISanion interaction. The -NO2 group promotes a larger effect relative to the -CF3 ligand. The -NO2 ligand positioned at the largest distance conceivable to the benzene-NH group promotes the lowest interference in the N-HMIDLINE HORIZONTAL ELLIPSISCl- interaction. These results provide information to design receptors with a larger capability to recognize anions.
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CoordenacAo de Aperfeicoamento de Pessoal de Nivel Superior - Brasil (CAPES) Finance 001 Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) 2011/07623-8 2017/24856-2 2019/19175-1 National Council for Scientific and Technological Development (CNPq) 313648/2018-2 Foundation for Research Support of the State of Rio Grande do Sul (FAPERGS) National Council for Scientific and Technological Development (CNPq) 306297/2018-3 430364/2018-0 LabEx CALSIMLAB ANR-11-LABX-0037-01 ANR-11-IDEX-0004-02 Comision Nacional de Investigacion Cientifica y Tecnologica (CONICYT) CONICYT FONDECYT 1181121 Centers of Excellence with Basal/Conicyt Financing FB0807 National Council for Scientific and Technological Development (CNPq) 311963/2017-0
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URI: https://repositorio.uchile.cl/handle/2250/178832
DOI: 10.1039/d0nj03685d
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New Journal of Chemistry Volumen: 44 Número: 41 Páginas: 17831-17839 Nov 2020
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