Diarylamines with the Neighboring Pyridyl Group: Synthesis and Modulation of the Amine Functionality via Intramolecular H-Bonding

Oleg A. Levitskiy; Ivan A. Klimchuk; Yuri K. Grishin; Vitaly A. Roznyatovsky; Boris N. Tarasevich; Tatiana V. Magdesieva

doi:10.1055/a-1683-0315

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(06): 1601-1612
DOI: 10.1055/a-1683-0315

paper

Diarylamines with the Neighboring Pyridyl Group: Synthesis and Modulation of the Amine Functionality via Intramolecular H-Bonding

Oleg A. Levitskiy

^aLomonosov Moscow State University, Dept. of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russian Federation

,

Ivan A. Klimchuk

^aLomonosov Moscow State University, Dept. of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russian Federation

,

Yuri K. Grishin

^aLomonosov Moscow State University, Dept. of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russian Federation

,

Vitaly A. Roznyatovsky

^aLomonosov Moscow State University, Dept. of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russian Federation

,

Boris N. Tarasevich

^aLomonosov Moscow State University, Dept. of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russian Federation

,

Tatiana V. Magdesieva ∗

^aLomonosov Moscow State University, Dept. of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russian Federation

^bNational Research University Higher School of Economics, Miasnitskaya Str. 20, Moscow 101000, Russian Federation

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Abstract

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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.

Key words

intramolecular H-bond - diarylamines - amination - voltammetric testing - antioxidants

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Referenzen

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