The anionic recognition mechanism based on polyol and boronic acid receptors

Author(s)

Orenha, Renato Pereira ^[1] ; Cintra, Claudia Haber ^[1] ; Peixoto, Leticia Bermudes ^[1] ; da Silva, Eder Henrique ^[1] ; Caramori, Giovanni Finoto ^[2] ; Ortolan, Alexandre Osmar ^[2] ; Piotrowski, Mauricio Jeomar ^[3] ; Tame Parreira, Renato Luis ^[1]

Affiliation

^[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

• Document type: Journal article
• Source: NEW JOURNAL OF CHEMISTRY; v. 44, n. 14, p. 5564-5571, APR 14 2020.
• Web of Science Citations: 0

Abstract

Anion selective recognition plays pivotal roles in the environmental field. The polyol and boronic acid receptor classes are investigated here to recognize the chloride (Cl-); fluoride (F-); dihydrogen phosphate (H2PO4-); acetate (AcO-); bromide (Br-); and hydrogen sulfate (HSO4-) anions. Energy Decomposition Analysis (EDA) shows that the anion-receptor interactions are predominantly electrostatic. Interestingly, the increase of the number of -CF3 groups or of the carbonic chain in the polyol structure favors Cl- recognition. The polyol-Cl- interactions are more attractive than the boronic acid-Cl- bond. Boronic acid recognizes F- and H2PO4- with the most attractive energies. The Quantum Theory of Atoms in Molecules (QTAIM) method elucidated that the recognition of AcO-, Cl-, Br-, and HSO4- by the receptors is maintained through hydrogen bonds, while the recognition of F- and H2PO4- by boronic acid involves BMIDLINE HORIZONTAL ELLIPSISF- and BMIDLINE HORIZONTAL ELLIPSISO--P bonds, respectively, showing a larger covalent character compared to other boronic acid-anion bonds, but with a primarily electrostatic nature. (AU)

• 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