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

Vazdar, Katarina; Kunetskiy, Roman; Saame, Jaan; Kaupmees, Karl; Leito, Ivo; Jahn, Ullrich (2014) Very Strong Organosuperbases Formed by Combining Imidazole and Guanidine Bases: Synthesis, Structure, and Basicity. Angewandte Chemie. International edition, 53 (5). pp. 1435-1438. ISSN 1433-7851

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Abstract

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 pKa values are determined as 26.1–29.3 in THF. They are thus probably the strongest phosphorous-free organic bases both in solution and in the gas phase. Calculations help to determining the structural and electronic factors giving rise to the high basicity.

Item Type: Article
Uncontrolled Keywords: guanidine ; organosuperbases ; synthetic methods ; basicity ; UV/Vis spectroscopy
Subjects: NATURAL SCIENCES > Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Physical Chemistry
Projects:
Project titleProject leaderProject codeProject type
Amino-beta-Lactams - Synthons for Biologically Interesting Compounds (Amino-beta-laktami - intermedijari u sintezi biološki interesantnih spojeva)-Vlasta Tomašić098-0982915-2948MZOS
Depositing User: Katarina Vazdar
Date Deposited: 30 Nov 2015 14:33
Last Modified: 30 Nov 2015 15:41
URI: http://fulir.irb.hr/id/eprint/2335
DOI: 10.1002/anie.201307212

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