Literature DB >> 24339377

Very strong organosuperbases formed by combining imidazole and guanidine bases: synthesis, structure, and basicity.

Katarina Vazdar1, Roman Kunetskiy, Jaan Saame, Karl Kaupmees, Ivo Leito, Ullrich Jahn.   

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 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.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  UV/Vis spectroscopy; basicity; guanidine; organosuperbases; synthetic methods

Year:  2013        PMID: 24339377     DOI: 10.1002/anie.201307212

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

1.  pH-dependent transient conformational states control optical properties in cyan fluorescent protein.

Authors:  Elena N Laricheva; Garrett B Goh; Alex Dickson; Charles L Brooks
Journal:  J Am Chem Soc       Date:  2015-02-18       Impact factor: 15.419

2.  Higher-Order Cyclopropenimine Superbases: Direct Neutral Brønsted Base Catalyzed Michael Reactions with α-Aryl Esters.

Authors:  Eric D Nacsa; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2015-08-04       Impact factor: 15.419

3.  Critical Aspects of Heme-Peroxo-Cu Complex Structure and Nature of Proton Source Dictate Metal-O(peroxo) Breakage versus Reductive O-O Cleavage Chemistry.

Authors:  Suzanne M Adam; Isaac Garcia-Bosch; Andrew W Schaefer; Savita K Sharma; Maxime A Siegler; Edward I Solomon; Kenneth D Karlin
Journal:  J Am Chem Soc       Date:  2016-12-28       Impact factor: 15.419

4.  Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base.

Authors:  Seulchan Lee; Si Ae Kim; Hye-Young Jang
Journal:  ACS Omega       Date:  2019-10-15

5.  Design of non-ionic carbon superbases: second generation carbodiphosphoranes.

Authors:  Sebastian Ullrich; Borislav Kovačević; Björn Koch; Klaus Harms; Jörg Sundermeyer
Journal:  Chem Sci       Date:  2019-08-16       Impact factor: 9.825

  5 in total

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