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Formation of the amide or ester bond is a crucial step in synthesis of numerous organic molecules, particularly peptides. The most valuable methods involve the coupling reagents activating carboxylic function directly in the reaction media. After two decades of domination of benzotriazole based chemistry, a new type of coupling reagents has been proposed [1, 2]. The latest development in so called molecular coupling reagents are N-triazinylammonium salts, especially those comprising quaternary morpholinium nitrogen atom [3]. Simple chlorides undergo substantial degradation during the storage. To explain high stability and excellent performance of tetrafluoroborates as molecular coupling reagents, we have studied several N-tiazynylammonium salts as well as their demetylated products by X-ray method. To our surprise no crystal structure of similar salt has been found in the literature.

Structural basis for superiority of quaternaryN-triazynylammonium tetrafluoroborates as new coupling reagents in peptide synthesis