Cyclic voltammetric studies on nitrosubstituted N(thioacyl)piperidines and morpholines

Add time:08/27/2019    Source:sciencedirect.com

Cyclic voltammograms in dimethylsulphoxide (DMSO) are presented and discussed for para- and meta-nitro-substituted N(thiobenzoyl)piperidines (1a, 2a) and morpholines (lb,2b) as well as for the corresponding N(thiocinnamoyl) derivatives (3b, 4a, b). In the first cycle, two main reduction waves (A, B) were found for compounds 1a, b, 3b, 4a, b, and only one (A) for 2a, b. In the second cycle, a new wave (D) appears at a potential less negative than A, indicating the formation of a new redox system.The electrochemial data were interpreted in terms of the following EECE mechanism; The species P− obtained during the reduction of 3b was unambiguously identified by means of ESR spectroscopy as the anion radical of p-nitrobenzaldehyde. For 1a, b it was assumed on similar grounds that P− is the p-nitrobenzoate anion radical.The formation of these species is accounted for by the chemical reaction of the dianion with the residual water present in the solvent.

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