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Polyradical PROXYL/TEMPO-Derived Amides: Synthesis, Physicochemical Studies, DFT Calculations, and Antimicrobial Activity.
ChemPlusChem ( IF 3.4 ) Pub Date : 2017-11-01 , DOI: 10.1002/cplu.201700343
Patrik Poprac 1 , Peter Poliak 1 , Miroslav Kavala 1 , Zuzana Barbieriková 1 , Michal Zalibera 1 , Marek Fronc 1 , Ľubomír Švorc 1 , Zuzana Vihonská 1 , Petra Olejníková 1 , Karol Lušpai 1 , Vladimír Lukeš 1 , Vlasta Brezová 1 , Peter Szolcsányi 1
Affiliation  

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.

中文翻译:

聚自由基PROXYL / TEMPO衍生的酰胺:合成,理化研究,DFT计算和抗菌活性。

合成了一系列具有2,2,5,5-四甲基-1-吡咯烷基氧基(PROXYL)和/或2,2,6,6-四甲基-1-哌啶基氧基(TEMPO)单元的聚硝基氧酰胺,并通过各种桥连接性能进行了分析。EPR光谱学提供了对其顺磁性特征和相关特性的详细了解。彻底检查有机溶剂中二硝基氧化物的EPR光谱可提供有关分子内运动,热力学和自旋交换机制的有价值的信息。对溶解的二硝基氧化物的低温X波段和Q波段EPR谱的分析提供了自旋-自旋距离,该距离可与DFT获得的理论值相媲美。循环伏安法研究揭示了PROXYL衍生的双基自由基的(准)可逆电化学行为,而发现含有TEMPO的双自由基和多自由基的可逆性显着降低。评估了氮氧化物对模型细菌,酵母和丝状真菌的抑制活性。
更新日期:2017-10-20
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