Studies of the Functionalized α-Hydroxy-p-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond
Molecules 2024
Anastasija Gaile, Sergejs Beļakovs, Ramona Dūrena, Ņikita Griščenko, Anzelms Zukuls, Nelli Batenko

In this work, reactions between 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-diones with different benzohydrazides were studied. Nucleophilic substitution at C(6) was followed by isomerization and led to α-hydroxy-p-quinone imine derivatives. Synthesized compounds represent a combination of several structural motifs: a benzimidazole core fused with α-hydroxy-p-quinone imine, which contains a benzamide fragment. X-ray crystallography analysis revealed the formation of dimers linked through OH···O interactions and stabilization of the imine form by strong intramolecular NH···N hydrogen bonds. The protonation/deprotonation processes were investigated in a solution using UV–Vis spectroscopy and a 1H NMR titration experiment. Additionally, the electrochemical properties of 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione and its α-hydroxy-p-quinone imine derivative as cathode materials were investigated in acidic and neutral environments using cyclic voltammetry measurements. Cathode material based on 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione could act as a potentially effective active electrode in aqueous electrolyte batteries; however, further optimization is required.


Atslēgas vārdi
hydrogen bonding | NMR titration | quinone | quinone imine | redox | X-ray crystallography
DOI
10.3390/molecules29071613
Hipersaite
https://www.mdpi.com/1420-3049/29/7/1613

Gaile, A., Beļakovs, S., Dūrena, R., Griščenko, Ņ., Zukuls, A., Batenko, N. Studies of the Functionalized α-Hydroxy-p-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond. Molecules, 2024, Vol. 29, No. 7, Article number 1613. e-ISSN 1420-3049. Pieejams: doi:10.3390/molecules29071613

Publikācijas valoda
English (en)
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