| Full text | |
| Author(s): |
Orenha, Renato Pereira
;
da Silva, Vanessa Borges
;
Caramori, Giovanni Finoto
;
de Souza Schneider, Felipe Silveira
;
Piotrowski, Mauricio Jeomar
;
Contreras-Garcia, Julia
;
Cardenas, Carlos
;
Briese Goncalves, Marina
;
Mendizabal, Fernando
;
Parreira, Renato Luis Tame
Total Authors: 10
|
| Document type: | Journal article |
| Source: | NEW JOURNAL OF CHEMISTRY; v. 44, n. 41, p. 9-pg., 2020-11-07. |
| 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. (AU) | |
| FAPESP's process: | 19/19175-1 - 5th School of Computational Chemistry - "Modeling in Supramolecular Chemistry" |
| Grantee: | Renato Luis Tame Parreira |
| Support Opportunities: | Organization Grants - Scientific Meeting |
| FAPESP's process: | 11/07623-8 - The use of quantum-mechanical methods to study the bonds and chemical interactions in self-organizing systems with applications in catalysis, medicinal chemistry, electrochromism, energy storage and conversion |
| Grantee: | Renato Luis Tame Parreira |
| Support Opportunities: | Research Grants - Young Investigators Grants |
| FAPESP's process: | 17/24856-2 - The Mechanism of the Substitution Reaction of the Ligand Nitrosyl by Aqua in Ruthenium Coordination Compounds |
| Grantee: | Renato Pereira Orenha |
| Support Opportunities: | Scholarships in Brazil - Post-Doctoral |