Pyridine‐Containing Donor‐Acceptor Diarylnitroxides: Noncovalent Stabilization of the Redox States
Publication type: Journal Article
Publication date: 2021-12-29
PubMed ID:
34967145
General Chemistry
Abstract
A series of new pyridyl- or 2-pyridyloxide-containing donor-acceptor diarylnitroxides was obtained and characterized; high stability of the ortho-2-pyridyl-containing diarylnitroxides was determined by kinetic measurements (τ1/2 =1733 h in benzene). Comparative voltammetric study of new nitroxides and their analog in which the Py replaces the Ph group revealed both through-bond and through-space stabilization of the NO redox states with the pyridyl/ 2-pyridyloxide moiety, providing reversibility of both oxidation and reduction processes. Adaptive conformational behavior of new pyridyl/pyridyloxide containing nitroxides upon one-electron oxidation and reduction was confirmed by DFT calculations. Stimuli-responsive conformational changes allow switching on/off dispersion and electrostatic interactions within the molecule and increase stability of the redox states. Spectroelectrochemical measurements provided experimental evidence for reversibility of the through-space stabilization of the oxidized state of the nitroxides with the neighboring pyridine lone pair.
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Levitskiy O. A. et al. Pyridine‐Containing Donor‐Acceptor Diarylnitroxides: Noncovalent Stabilization of the Redox States // ChemPlusChem. 2021. Vol. 87. No. 3.
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Levitskiy O. A., Bogdanov A. V., Klimchuk I. A., Magdesieva T. V. Pyridine‐Containing Donor‐Acceptor Diarylnitroxides: Noncovalent Stabilization of the Redox States // ChemPlusChem. 2021. Vol. 87. No. 3.
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TY - JOUR
DO - 10.1002/cplu.202100508
UR - https://doi.org/10.1002/cplu.202100508
TI - Pyridine‐Containing Donor‐Acceptor Diarylnitroxides: Noncovalent Stabilization of the Redox States
T2 - ChemPlusChem
AU - Levitskiy, Oleg A
AU - Bogdanov, Alexey V
AU - Klimchuk, Ivan A
AU - Magdesieva, Tatiana V.
PY - 2021
DA - 2021/12/29
PB - Wiley
IS - 3
VL - 87
PMID - 34967145
SN - 2192-6506
ER -
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@article{2021_Levitskiy,
author = {Oleg A Levitskiy and Alexey V Bogdanov and Ivan A Klimchuk and Tatiana V. Magdesieva},
title = {Pyridine‐Containing Donor‐Acceptor Diarylnitroxides: Noncovalent Stabilization of the Redox States},
journal = {ChemPlusChem},
year = {2021},
volume = {87},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/cplu.202100508},
number = {3},
doi = {10.1002/cplu.202100508}
}