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Type: Artigo
Title: Analysis of solvent-accessible voids and proton-coupled electron transfer of 2,6-bis(1H-imidazol-2-yl)pyridine and its hydrochloride
Author: Guerra, Renan B.
Huamani, Luis S. C.
Tenorio, Juan C.
Guimaraes, Willian M.
Bonacin, Juliano A.
Barboza Formiga, Andre Luiz
Abstract: The crystal structures of the solid form of solvated 2,6-bis(1H-imidazol-2-yl)pyridine (H(2)dimpy) trihydrate, C11H9N5 center dot 3H(2)O center dot[+solvent], I, and its hydrate hydrochloride salt 2-[6-(1H-imidazol-2-yl)pyridin-2-yl]-1H-imidazol-3-ium chloride trihydrate, C11H10N5+center dot Cl-center dot 3H(2)O, II, are reported and analysed in detail, along with potentiometric and spectrophotometric titrations for evaluation of the acid-base equilibria and proton-coupled electron-transfer reactions. Compound I crystallizes in the high-symmetry trigonal space group P3(2)21 with an atypical formation of solvent-accessible voids, as a consequence of the 3(2) screw axis in the crystallographic c-axis direction, which are probably occupied by uncharacterized disordered solvent molecules. Additionally, the trihydrated chloride salt crystallizes in the conventional monoclinic space group P2(1)/c without the formation of solvent-accessible voids. The acid-base equilibria of H(2)dimpy were studied by potentiometric and spectrophotometric titrations, and the results suggest the formation of H(3)dimpy(+) (pK(a1) = 5.40) and H(4)dimpy(2+) (pK(a2) = 3.98), with the electrochemical behaviour of these species showing two consecutive irreversible proton-coupled electron-transfer reactions. Density functional theory (DFT) calculations corroborate the interpretation of the experimental results and support the assignment of the electrochemical behaviour
Subject: Estrutura de cristal
Country: Estados Unidos
Editor: Wiley-Blackwell
Rights: Aberto
Identifier DOI: 10.1107/S2053229619011951
Date Issue: 2019
Appears in Collections:IQ - Artigos e Outros Documentos

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