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

0429647 - ÚOCHB 2015 RIV DE eng J - Článek v odborném periodiku
Vazdar, Katarina - Kunetskiy, Roman Alexejevič - Saame, J. - Kaupmees, K. - Leito, I. - Jahn, Ullrich
Very Strong Organosuperbases Formed by Combining Imidazole and Guanidine Bases: Synthesis, Structure, and Basicity.
Angewandte Chemie - International Edition. Roč. 53, č. 5 (2014), s. 1435-1438. ISSN 1433-7851. E-ISSN 1521-3773
Institucionální podpora: RVO:61388963
Klíčová slova: guanidine * organosuperbases * synthetic methods * basicity * UV/Vis spectroscopy
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 11.261, rok: 2014

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(alpha) 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.
Trvalý link: http://hdl.handle.net/11104/0234755