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Issue 41, 2019

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

Supplementary files

Article information


Submitted
18 Jul 2019
Accepted
15 Aug 2019
First published
16 Aug 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 9483-9492
Article type
Edge Article

Design of non-ionic carbon superbases: second generation carbodiphosphoranes

S. Ullrich, B. Kovačević, B. Koch, K. Harms and J. Sundermeyer, Chem. Sci., 2019, 10, 9483 DOI: 10.1039/C9SC03565F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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