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(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

Role of Protonation and Isomerism in the Supramolecular Architectures of Heteroaryl-2-imidazole Compounds: Crystal Packing Patterns and Energetics

Texto completo
Autor(es):
Santa Cruz Huamani, Luis Enrique [1] ; Tenorio, Juan Carlos [1] ; Guerra, Renan Barrach [1] ; Nakahata, Douglas Hideki [1] ; Bibi, Naheed [1] ; Bonacin, Juliano Alves [1] ; Barboza Formiga, Andre Luiz [1]
Número total de Autores: 7
Afiliação do(s) autor(es):
[1] Univ Estadual Campinas, UNICAMP, Dept Inorgan Chem, BR-13083970 Campinas, SP - Brazil
Número total de Afiliações: 1
Tipo de documento: Artigo Científico
Fonte: Crystal Growth & Design; v. 20, n. 8, p. 5143-5159, AUG 5 2020.
Citações Web of Science: 1
Resumo

The influence of isomerism and protonation on crystal packing patterns of three isomeric heteroaryl-2-imidazoles and one related compound was investigated by using single-crystal X-ray diffraction and density functional theory. The comparison of their crystal structures helped unveil the details of the energetic balance controlling supramolecular packing and an unprecedented supramolecular synthon. The neutral species were featured by a whole crystal close packing like a herringbone pattern, which was mainly favored by C-H center dot center dot center dot pi interactions. On the other hand, the crystal packing of the protonated species was characterized by pi-stacking layers being supported by pi center dot center dot center dot pi and anion-pi interactions. Energy framework analysis revealed that both Coulombic interactions between hydrogen bond chains and dispersion energies mainly contributed to the stabilization of the herringbone pattern assembly, whereas a predominant contribution from Coulombic energy frameworks to total energy in protonated forms was observed. The different patterns displayed pieces of evidence of not only the important participation of the heteroaryl moieties in the supramolecular assembly but also the significant contribution of protonation hampering the N-H center dot center dot center dot N hydrogen bonding interactions in the imidazole group. A thorough characterization of the compounds by means of thermogravimetric analysis, differential scanning calorimetry, Fourier-transform infrared spectroscopy, NMR, and electrospray ionization-(+)-MS is also presented. (AU)

Processo FAPESP: 15/20882-3 - Complexos metálicos com sulfametoxidiazina e sulfadimetoxina: síntese, caracterização e aplicações como agentes antimicrobianos para uso tópico
Beneficiário:Douglas Hideki Nakahata
Linha de fomento: Bolsas no Brasil - Doutorado
Processo FAPESP: 14/50906-9 - INCT 2014: em Materiais Complexos Funcionais (INOMAT)
Beneficiário:Fernando Galembeck
Linha de fomento: Auxílio à Pesquisa - Temático
Processo FAPESP: 13/22127-2 - Desenvolvimento de novos materiais estratégicos para dispositivos analíticos integrados
Beneficiário:Lauro Tatsuo Kubota
Linha de fomento: Auxílio à Pesquisa - Temático
Processo FAPESP: 17/23960-0 - Estudo de mecanismo de oxidação de água por catalisadores operando em pH=7 e sua incorporação em eletrodos impressos em 3D
Beneficiário:Juliano Alves Bonacin
Linha de fomento: Auxílio à Pesquisa - Regular