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The phosphoryl compound (O:)P(TMG) 3  (TMG = N’,N’,N”,N”-tetramethylguanidyl) (6) was synthesized during attempts to obtain the potentially very basic (but still unknown) compound P(TMG) 3  (1). Its reaction with HCl resulted in the triply protonated species 7. The crystal structure of compound 7 was determined; it crystallizes as a bis-dichloromethane solvate. Each protonated nitrogen forms a hydrogen bond to one chloride. A series of protonation experiments was conducted in order to test the behaviour of 6 towards weak acids.

Tris-N-(N′,N′,N″,N″-tetramethylguanidyl)phosphine Oxide – Synthesis and Reaction with Acids