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Zwitterionic form of Ugi amine H-phosphinic acid: Structure and electrochemical properties

Abstract Ugi amine H-phosphinic acid was prepared by hydrolysis of 1-dichlorophosphanyl-2-N,N-dimethylaminomethylferrocene (1). The formation of the zwitterionic form of Ugi amine H-phosphinic acid (2) was clearly demonstrated by NMR, X-ray… Click to show full abstract

Abstract Ugi amine H-phosphinic acid was prepared by hydrolysis of 1-dichlorophosphanyl-2-N,N-dimethylaminomethylferrocene (1). The formation of the zwitterionic form of Ugi amine H-phosphinic acid (2) was clearly demonstrated by NMR, X-ray single crystal diffraction studies and electrochemical measurements. It was shown for the first time that Ugi amine H-phosphinic acid, unlike other monophosphinates reported in the literature, does not show double oxidation peaks, which clearly indicates the presence of a single form in solution. It is shown that the oxidative potential of 2 is more positive than that of other monophosphinates, since in solution the substance exists completely in the zwitterionic form.

Keywords: amine phosphinic; ugi amine; form; phosphinic acid

Journal Title: Electrochemistry Communications
Year Published: 2021

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