Premium
Very Strong Organosuperbases Formed by Combining Imidazole and Guanidine Bases: Synthesis, Structure, and Basicity
Author(s) -
Vazdar Katarina,
Kunetskiy Roman,
Saame Jaan,
Kaupmees Karl,
Leito Ivo,
Jahn Ullrich
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201307212
Subject(s) - imidazole , guanidine , chemistry , gas phase , computational chemistry , crystallography , stereochemistry , organic chemistry
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 ′‐ b is( i midazolyl) g uanidine bases (BIG bases) is reported. Their p K α 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.