Literature DB >> 12010050

Basicity of a stable carbene, 1,3-di-tert-butylimidazol-2-ylidene, in THF.

Yeong-Joon Kim1, Andrew Streitwieser.   

Abstract

The basicity of 1,3-di-tert-butylimidazol-2-ylidene (1) was measured in THF against three hydrocarbon indicators. Both ion pairs and free ions were found and the corresponding equilibrium constants were measured. Homoconjugation was not found in either THF or DMSO. The carbene is effectively more basic in DMSO by several pK units, probably because of hydrogen bonding of 1-H(+) to DMSO. Model ab initio computations are consistent with these results.

Entities:  

Year:  2002        PMID: 12010050     DOI: 10.1021/ja025628j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  14 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

2.  Experimental and Computational Gas Phase Acidities of Conjugate Acids of Triazolylidene Carbenes: Rationalizing Subtle Electronic Effects.

Authors:  Yijie Niu; Ning Wang; Alberto Muñoz; Jiahui Xu; Hao Zeng; Tomislav Rovis; Jeehiun K Lee
Journal:  J Am Chem Soc       Date:  2017-10-17       Impact factor: 15.419

3.  Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors:  Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

4.  Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes.

Authors:  Yves Canac; Salvador Conejero; Michèle Soleilhavoup; Bruno Donnadieu; Guy Bertrand
Journal:  J Am Chem Soc       Date:  2006-01-18       Impact factor: 15.419

5.  N-heterocyclic carbene-catalyzed conjugate additions of alcohols.

Authors:  Eric M Phillips; Matthias Riedrich; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

6.  A cooperative N-heterocyclic carbene/chiral phosphate catalysis system for allenolate annulations.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-04       Impact factor: 15.336

7.  New synthetic routes to C-amino phosphorus ylides and their subsequent fragmentation into carbenes and phosphines.

Authors:  Salvador Conejero; Maoying Song; David Martin; Yves Canac; Michele Soleilhavoup; Guy Bertrand
Journal:  Chem Asian J       Date:  2006-07-17

8.  Convenient preparation of high molecular weight poly(dimethylsiloxane) using thermally latent NHC-catalysis: a structure-activity correlation.

Authors:  Stefan Naumann; Johannes Klein; Dongren Wang; Michael R Buchmeiser
Journal:  Beilstein J Org Chem       Date:  2015-11-20       Impact factor: 2.883

9.  Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalyst.

Authors:  Jiean Chen; Sixuan Meng; Leming Wang; Hongmei Tang; Yong Huang
Journal:  Chem Sci       Date:  2015-04-23       Impact factor: 9.825

Review 10.  Asymmetric Michael Addition Mediated by Chiral Ionic Liquids.

Authors:  Yumiko Suzuki
Journal:  Mini Rev Org Chem       Date:  2018-06       Impact factor: 2.495

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