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- Title
Polyradical PROXYL/TEMPO-Derived Amides: Synthesis, Physicochemical Studies, DFT Calculations, and Antimicrobial Activity.
- Authors
Poprac, Patrik; Poliak, Peter; Kavala, Miroslav; Barbieriková, Zuzana; Zalibera, Michal; Fronc, Marek; Švorc, Ľubomír; Vihonská, Zuzana; Olejníková, Petra; Lušpai, Karol; Lukeš, Vladimír; Brezová, Vlasta; Szolcsányi, Peter
- Abstract
A series of polynitroxide amides possessing 2,2,5,5-tetramethyl-1-pyrrolidinyloxy (PROXYL) and/or 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) units connected through various bridges were synthesized and their properties were analyzed. EPR spectroscopy provided detailed insight into their paramagnetic character and related properties. A thorough examination of the EPR spectra of dinitroxides in organic solvents provided valuable information on the intramolecular motions, thermodynamics, and spin-exchange mechanisms. Analysis of low-temperature X- and Q-band EPR spectra of the dissolved dinitroxides provided spin-spin distances that were comparable with the theoretical values obtained by DFT. Cyclic voltammetry investigations revealed (quasi)reversible electrochemical behavior for PROXYL-derived biradicals, whereas significant loss of the reversibility was found for TEMPO-containing bi- and polyradicals. The inhibitory activities of the nitroxides against model bacteria, yeasts, and filamentous fungi were assessed.
- Subjects
TETRAMETHYL compounds; AMIDE synthesis; DENSITY functional theory; ELECTRON paramagnetic resonance spectroscopy; ORGANIC solvents; SPIN exchange; NITROXIDES; FILAMENTOUS fungi
- Publication
ChemPlusChem, 2017, Vol 82, Issue 11, p1326
- ISSN
2192-6506
- Publication type
Article
- DOI
10.1002/cplu.201700343