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Synthesis 2022; 54(06): 1601-1612
DOI: 10.1055/a-1683-0315
DOI: 10.1055/a-1683-0315
paper
Diarylamines with the Neighboring Pyridyl Group: Synthesis and Modulation of the Amine Functionality via Intramolecular H-Bonding
This work was supported by the Russian Science Foundation (Project number 19-13-00094). The NMR part of this work was supported by M.V. Lomonosov Moscow State University Program of Development.
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1683-0315.
- Supporting Information
Publication History
Received: 03 August 2021
Accepted after revision: 29 October 2021
Accepted Manuscript online:
29 October 2021
Article published online:
29 November 2021
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