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JOURNALS // Mendeleev Communications // Archive

Mendeleev Commun., 2024 Volume 34, Issue 5, Pages 676–679 (Mi mendc217)

Communications

Competition between n → π* interactions and H-bonding: a way to stabilize aminoxyl anions and to improve electron transfer kinetics

O. A. Levitskiy, A. V. Bogdanov, T. V. Magdesieva

Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation

Abstract: A new approach to stabilization of the reduced state of nitroxides in solution is suggested. Thermodynamic stabilization of the strongly basic aminoxyl anions toward protonation and hydrogen bond formation with the solvent was achieved by intramolecular n → π* interactions. A new stable nitroxide radical bearing ortho-acyl group was synthesized to demonstrate this effect by means of cyclic voltammetry.

Keywords: intramolecular n → π* interactions, anion stabilization, diaryl nitroxides, hydrogen bonding, voltammetric testing.

Language: English

DOI: 10.1016/j.mencom.2024.09.016



© Steklov Math. Inst. of RAS, 2025