The alkaline earth t-butylthiolates of Sr and Ba dissolve in N-methyl-2-pyrrolidone (NMP) normally. However, the Ca complex forms a blue solution that over time forms crystals of a calcium salt of a unique dianion (shown below) that results from the addition of sulfur to the NMP ring, joining two NMP rings together, and the loss of multiple hydrogen atoms. The dianion is planar and presumably aromatic. We hypothesize that the Ca<sup>2+</sup> ion somehow templates the formation of this unusual anion. Additional experimental details, efforts to make the dianion more deliberately, and calculations of its energy levels based on density functional theory will be described.

Synthesis and structure of a unique dianion derived from N-methyl-2-pyrrolidone

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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