Complementary Effect of Intra- and Intermolecular Hydrogen Bonds on Electron Transfer in β-Hydroxy-Anthraquinone Derivatives
| Autor: | Noriko Okumura, Tatsushi Nakayama, Bunji Uno |
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| Rok vydání: | 2020 |
| Předmět: |
Steric effects
010304 chemical physics Hydrogen bond Intermolecular force Substituent 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Surfaces Coatings and Films Quinone chemistry.chemical_compound Electron transfer chemistry 0103 physical sciences Materials Chemistry Moiety Physical and Theoretical Chemistry Inductive effect |
| Zdroj: | The journal of physical chemistry. B. 124(5) |
| ISSN: | 1520-5207 |
| Popis: | We have carried out an electrochemical and theoretical study on the relationship between electron transfer (ET) and hydrogen bonding in 11 different 9,10-anthraquinone (AQ) derivatives, including β-hydroxy AQs and their methoxylated analogs, in the presence of hydrogen donors in acetonitrile (ACN). The complementary effects of the intra- and intermolecular hydrogen bonds (HBs) on ET were studied by analyzing the complex formation constants derived from the intermolecular HB. Our results revealed that the inductive effect of the β substituent that indirectly controls the charge distribution on the AQ carbonyl oxygen, and steric hindrance at the β position, affect the complex formation constants. Furthermore, the analysis of ET in different isomeric dihydroxy AQs suggested that the position of the hydroxy groups affects the charge distribution and stabilizes structures through conjugation of the quinone moiety including the ipso ring, controlling the intra- and intermolecular HBs complementarily. |
| Databáze: | OpenAIRE |
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