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Abstract
Abstract A series of alkali metal salts of dithiocarbamate‐substituted carboxylate (DTCC) anions were prepared by reaction of the parent amino acids with carbon disulfide and an alkali metal hydroxide. The target compounds, which were isolated in anhydrous form or as hydrates, were extensively characterized by elemental analyses, IR and NMR spectroscopy, thermal analyses, cyclic voltammetry, and single‐crystal X‐ray diffraction. The isolated compounds are more or less hygroscopic and display a varying dehydratization and decomposition behavior upon heating. The assumed degradation of the DTCC scaffold was found to depend on the substitution pattern as well as on the alkali metal counterion, and covers a range between 200 and 340 °C. In aqueous solution, the DTCC anions show irreversible electrochemical oxidations, where the corresponding redox potentials are governed by the substitution pattern of the nitrogen atom. Single‐crystal structural analyses of sodium and potassium derivatives revealed that these compounds exist as two‐ or three‐dimensional coordination polymers in the solid state, with the alkali‐metal ions adopting typical irregular coordination environments with coordination numbers of six or higher.
Highlights
Dithiocarbamate-substitued carboxylates (DTCCs) are relevant in different fields of research, including biomedical chemistry[1–3] and material sciences.[4–6] dithiocarbamate-substituted carboxylate (DTCC) salts can be used as flotation agents for ore mining.[7]
In order to obtain a detailed picture about alkali metal DTCCs, we report here the preparation and extensive characterization of Li, Na, and K salts of DTCC anions derived from selected amino acids
Summarizing the results reported here, we investigated the synthesis and properties of lithium, sodium, and potassium salts with different dithiocarbamato-carboxylate (DTCC) anions, in order to reveal a complete picture of this widely useful class of compounds
Summary
Metal, alkaline-earth metal, or ammonium DTCC salts derived from natural α-amino acids have been reported throughout the 20th century.[15,16]. Even though these compounds are important intermediates for the preparation of metal complexes, they have been adequately characterized only in few cases. Among alkali metal DTCCs, the vast majority of known compounds are sodium and potassium derivatives, which have been isolated and characterized by NMR spectroscopy in only few studies.[4,16–18]. In order to obtain a detailed picture about alkali metal DTCCs, we report here the preparation and extensive characterization of Li, Na, and K salts of DTCC anions derived from selected amino acids. All compounds were characterized by IR and NMR spectroscopy as well as elemental analyses, and the solid-state structures of a series of compounds are reported. We investigated the thermal decomposition and redox properties of the compounds by thermal analyses and cyclic voltammetry, respectively
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