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

| Request a personal copy from author

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 title Project leader Project code Project type Amino-beta-Lactams - Synthons for Biologically Interesting Compounds (Amino-beta-laktami - intermedijari u sintezi biološki interesantnih spojeva)- Vlasta Tomašić 098-0982915-2948 MZOS
Depositing User:	Katarina Vazdar
Date Deposited:	30 Nov 2015 14:33
URI:	http://fulir.irb.hr/id/eprint/2335
DOI:	10.1002/anie.201307212

Actions (login required)

View Item