Very Strong Organosuperbases Formed by Combining Imidazole and Guanidine Bases: Synthesis, Structure, and Basicity

New structural motives for organosuperbases, that are easy to prepare and highly basic are urgently required in many areas of chemistry. The synthesis of N,N'-bis(imidazolyl)guanidine bases (BIG bases) is reported. Their pK sub(a) values are determined as 26.1-29.3 in THF. They are thus probabl...

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Bibliographic Details
Published in:Angewandte Chemie 2014-01, Vol.126 (5), p.1459-1462
Main Authors: Vazdar, Katarina, Kunetskiy, Roman, Saame, Jaan, Kaupmees, Karl, Leito, Ivo, Jahn, Ullrich
Format: Article
Language:English
Subjects:
Basicity
Electronics
Gas phases
Guanidines
Imidazole
Mathematical analysis
Synthesis
Online Access:Get full text
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Summary:New structural motives for organosuperbases, that are easy to prepare and highly basic are urgently required in many areas of chemistry. The synthesis of N,N'-bis(imidazolyl)guanidine bases (BIG bases) is reported. Their pK sub(a) values are determined as 26.1-29.3 in THF. They are thus probably the strongest known phosphorous-free organic bases both in solution and in the gas phase. Calculations help to determine the structural and electronic factors giving rise to the high basicity.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201307212