Details

Autor(en) / Beteiligte

• Vazdar, Katarina
• Kunetskiy, Roman
• Saame, Jaan
• Kaupmees, Karl
• Leito, Ivo
• Jahn, Ullrich

Titel

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

Ist Teil von

• Angewandte Chemie (International ed.), 2014-01, Vol.53 (5), p.1435-1438

Auflage

International ed. in English

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2014

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 pKα 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. Think BIG: Probably the strongest organic non‐phosphorus superbases, having pKα values of 26.1–29.3 in THF, are synthesized by combining imidazole and guanidine structural motifs to give N,N′‐bis(imidazolyl)guanidine bases (termed BIG bases). Their basicity was determined in solution by UV/Vis spectroscopy and in the gas phase by computational methods. The innovative design opens possibilities for the broader application of organosuperbases.