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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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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]
Total Authors: 7
[1] Univ Estadual Campinas, UNICAMP, Dept Inorgan Chem, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Crystal Growth & Design; v. 20, n. 8, p. 5143-5159, AUG 5 2020.
Web of Science Citations: 1

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)

FAPESP's process: 17/23960-0 - Study of the mechanism of water oxidation by catalysts operating at pH7 and its incorporation in electrodes printed in 3D
Grantee:Juliano Alves Bonacin
Support Opportunities: Regular Research Grants
FAPESP's process: 14/50906-9 - INCT 2014: in Functional Complex Materials
Grantee:Fernando Galembeck
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 15/20882-3 - Metal complexes of sulfamethoxydiazine and sulfadimethoxine: synthesis, characterization and applications as antimicrobial agents for topical use
Grantee:Douglas Hideki Nakahata
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 13/22127-2 - Development of novel materials strategic for integrated analytical devices
Grantee:Lauro Tatsuo Kubota
Support Opportunities: Research Projects - Thematic Grants