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- W3208131220 abstract "Abstract New pyridyl-containing diarylamines were obtained via Cu-assisted reductive amination of the ortho-2-pyridylarylboronic acids. Comparative analysis of the spectral and electrochemical data obtained for new diarylamines and their pyridyl-free counterparts revealed the intramolecular H-bond (IMHB) formation which significantly influences the properties of the amino group. The electron density at the N atom of the amino group is increased due to partial weakening of the N–H bond, although the BDE and activation energy for the H-atom abstraction is increased due to the chelating effect of two N atoms. The ortho-pyridyl-containing diarylamines are more prone to be oxidized as compared to their pyridyl-free counterparts; the shift in the oxidation potential values correlates with the strength of the intramolecular H-bonding which can be tuned by inserting substituents in the pyridyl or phenyl rings. The IMHB is reserved even in polar solvents having a significant H-acceptor ability (such as DMSO) but can be destroyed in methanol, testifying in favor of the dynamic nature of the H-bonding." @default.
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- W3208131220 date "2021-10-29" @default.
- W3208131220 modified "2023-10-13" @default.
- W3208131220 title "Diarylamines with the Neighboring Pyridyl Group: Synthesis and Modulation of the Amine Functionality via Intramolecular H-Bonding" @default.
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- W3208131220 doi "https://doi.org/10.1055/a-1683-0315" @default.
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