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Design of non-ionic carbon superbases: second generation carbodiphosphoranes

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Abstract

A new generation of carbodiphosphoranes (CDPs), incorporating pyrrolidine, tetramethylguanidine, or tris(dimethylamino)phosphazene as substituents is introduced as the most powerful class of non-ionic carbon superbases on the basicity scale to date. The synthetic approach as well as NMR spectroscopic and structural characteristics in the free and protonated form are described. Investigation of basicity in solution and in the gas phase by experimental and theoretical means provides the to our knowledge first reported pKBH+ values for CDPs in the literature and suggest them as upper tier superbases.

Graphical abstract: Design of non-ionic carbon superbases: second generation carbodiphosphoranes

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Publication details

The article was received on 18 Jul 2019, accepted on 15 Aug 2019 and first published on 16 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC03565F
Chem. Sci., 2019, Advance Article
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    Design of non-ionic carbon superbases: second generation carbodiphosphoranes

    S. Ullrich, B. Kovačević, B. Koch, K. Harms and J. Sundermeyer, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03565F

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