Unexpected formation of N,N′,N″-trialkylguanidinium bis(trifluoromethylsulfonyl)imide salts from carbodiimides and bis(trifluoromethylsulfonyl)imide

• Reaction of bis(trifluormethylsulfonyl)imide (HTFSI) with N,N′-dialkylcarbodiimides was studied.
• The products were shown to have the structure of N,N′,N″-trialkylguanidinium salts of TFSI.
• The ionic structure of the products was proved by measuring the conductivity in organic solvents.

Bis(trifluoromethylsulfonyl)imide (HTFSI) was found to react with diisopropyl- and dicyclohexylcarbodiimides with the formation of N,N′,N″-trialkylguanidinium TFSI salts. The ionic structure of the products is indicated by multinuclear NMR spectroscopy, quantum chemical calculations and by measuring ionic conductivity in organic solvents.

Dialkylcarbodiimides react with bis(trifluormethylsulfonyl)imide to give N,N′,N″-trialkylguanidinium salts via the transfer of one alkyl group from one molecule of carbodiimide to another. The ionic nature of the products is proved by NMR spectroscopy and by measuring the conductivity in solution.Figure optionsDownload as PowerPoint slide