Studies of the Functionalized α-Hydroxy-<i>p</i>-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond
In this work, reactions between 6,7-dichloropyrido[1,2-<i>a</i>]benzimidazole-8,9-diones with different benzohydrazides were studied. Nucleophilic substitution at C(6) was followed by isomerization and led to α-hydroxy-<i>p</i>-quinone imine derivatives. Synthesized compounds...
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MDPI AG
2024-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/7/1613 |
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| author | Anastasija Gaile Sergey Belyakov Ramona Dūrena Ņikita Griščenko Anzelms Zukuls Nelli Batenko |
| author_facet | Anastasija Gaile Sergey Belyakov Ramona Dūrena Ņikita Griščenko Anzelms Zukuls Nelli Batenko |
| author_sort | Anastasija Gaile |
| collection | DOAJ |
| description | In this work, reactions between 6,7-dichloropyrido[1,2-<i>a</i>]benzimidazole-8,9-diones with different benzohydrazides were studied. Nucleophilic substitution at C(6) was followed by isomerization and led to α-hydroxy-<i>p</i>-quinone imine derivatives. Synthesized compounds represent a combination of several structural motifs: a benzimidazole core fused with α-hydroxy-<i>p</i>-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 <sup>1</sup>H NMR titration experiment. Additionally, the electrochemical properties of 6,7-dichloropyrido[1,2-<i>a</i>]benzimidazole-8,9-dione and its α-hydroxy-<i>p</i>-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-<i>a</i>]benzimidazole-8,9-dione could act as a potentially effective active electrode in aqueous electrolyte batteries; however, further optimization is required. |
| first_indexed | 2024-04-24T10:39:00Z |
| format | Article |
| id | doaj.art-547d0bb342544396bd5309aafc833afb |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-24T10:39:00Z |
| publishDate | 2024-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-547d0bb342544396bd5309aafc833afb2024-04-12T13:23:34ZengMDPI AGMolecules1420-30492024-04-01297161310.3390/molecules29071613Studies of the Functionalized α-Hydroxy-<i>p</i>-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen BondAnastasija Gaile0Sergey Belyakov1Ramona Dūrena2Ņikita Griščenko3Anzelms Zukuls4Nelli Batenko5Institute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaLatvian Institute of Organic Chemistry, Aizkraukles Str. 21, LV-1006 Riga, LatviaInstitute of Materials and Surface Engineering, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaInstitute of Materials and Surface Engineering, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaInstitute of Materials and Surface Engineering, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaInstitute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaIn this work, reactions between 6,7-dichloropyrido[1,2-<i>a</i>]benzimidazole-8,9-diones with different benzohydrazides were studied. Nucleophilic substitution at C(6) was followed by isomerization and led to α-hydroxy-<i>p</i>-quinone imine derivatives. Synthesized compounds represent a combination of several structural motifs: a benzimidazole core fused with α-hydroxy-<i>p</i>-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 <sup>1</sup>H NMR titration experiment. Additionally, the electrochemical properties of 6,7-dichloropyrido[1,2-<i>a</i>]benzimidazole-8,9-dione and its α-hydroxy-<i>p</i>-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-<i>a</i>]benzimidazole-8,9-dione could act as a potentially effective active electrode in aqueous electrolyte batteries; however, further optimization is required.https://www.mdpi.com/1420-3049/29/7/1613quinonequinone iminehydrogen bondingX-ray crystallographyNMR titrationredox |
| spellingShingle | Anastasija Gaile Sergey Belyakov Ramona Dūrena Ņikita Griščenko Anzelms Zukuls Nelli Batenko Studies of the Functionalized α-Hydroxy-<i>p</i>-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond Molecules quinone quinone imine hydrogen bonding X-ray crystallography NMR titration redox |
| title | Studies of the Functionalized α-Hydroxy-<i>p</i>-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond |
| title_full | Studies of the Functionalized α-Hydroxy-<i>p</i>-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond |
| title_fullStr | Studies of the Functionalized α-Hydroxy-<i>p</i>-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond |
| title_full_unstemmed | Studies of the Functionalized α-Hydroxy-<i>p</i>-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond |
| title_short | Studies of the Functionalized α-Hydroxy-<i>p</i>-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond |
| title_sort | studies of the functionalized α hydroxy i p i quinone imine derivatives stabilized by intramolecular hydrogen bond |
| topic | quinone quinone imine hydrogen bonding X-ray crystallography NMR titration redox |
| url | https://www.mdpi.com/1420-3049/29/7/1613 |
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