Design of supramolecular systems capable of recognizing anions uniquely by aliphatic C-HMIDLINE HORIZONTAL ELLIPSISanion hydrogen bonds: theoretical insights

Autor(es)

Orenha, Renato Pereira ^[1] ; Cintra, Claudia Haber ^[1] ; Lucas Natal, Maria Laura ^[1] ; Colaco, Matheus Cachoeira ^[2] ; Caramori, Giovanni Finoto ^[2] ; Piotrowski, Mauricio Jeomar ^[3] ; Tame Parreira, Renato Luis ^[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

• Tipo de documento: Artigo Científico
• Fonte: NEW JOURNAL OF CHEMISTRY; v. 45, n. 41 SEP 2021.
• Citações Web of Science: 0

Resumo

Anions perform several important functions in biological processes. Thus, structures that are able to interact with anions are of great relevance. Here, light is shed on the main characteristics of the bonds between the anions chloride (Cl-), bromide (Br-) and nitrite (NO2-) and the -CH groups of trioxane structures non-substituted and polarized by the ligands (i) -CH3, (ii) -CH2Cl, (iii) -CHCl2, and (iv) -CCl3. There is a less attractive recognition of the anions Cl-, Br- and NO2- using trioxane substituted by the -CH3 groups compared to the receptors non-substituted due to the destabilization of the electrostatic interactions C-HMIDLINE HORIZONTAL ELLIPSIS(Cl-, Br- and NO2-). The presence of electron withdrawing groups in the receptor structure improves the interaction with the anions through more favorable sigma bonds between the -CH groups and anions Cl-, Br- and NO2-. The anion NO2- is recognized with (i) more favorable and (ii) similar energy and rate by receptors containing (i) -CH3 and (ii) -CH2Cl, -CHCl2 or -CCl3, compared to anions Cl- and Br-. The lower values of the Pauli repulsion contribution in receptorsMIDLINE HORIZONTAL ELLIPSISCl- bonds when compared to the interactions receptorsMIDLINE HORIZONTAL ELLIPSISBr- explain the more favorable recognition of the anion Cl- in relation to Br-. The larger recognition rate of the anion Cl- regarding to anion Br- is determined by more favorable electrostatic and orbital interactions. These data provide relevant information about the recognition of anions using C-H bonds and can be used to guide the development of new receptors. (AU)

• 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
• 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