Literature DB >> 21116519

pKas of the conjugate acids of N-heterocyclic carbenes in water.

Eleanor M Higgins1, Jennifer A Sherwood, Anita G Lindsay, James Armstrong, Richard S Massey, Roger W Alder, AnnMarie C O'Donoghue.   

Abstract

pK(a) values of 19.8-28.2 are reported for the conjugate acids of a large series of NHCs in water. The effects of ring size, N-substituent and C(4)-C(5) saturation on pK(a) are discussed.

Entities:  

Year:  2010        PMID： 21116519     DOI： 10.1039/c0cc03367g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  19 in total

1.  A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

Authors:  Kun Liu; M Todd Hovey; Karl A Scheidt
Journal:  Chem Sci       Date:  2014-10-01       Impact factor: 9.825

Review 2.  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

3.  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

4.  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

5.  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

6.  A cyclic diaminocarbene with a pyramidalized nitrogen atom: a stable N-heterocyclic carbene with enhanced electrophilicity.

Authors:  David Martin; Nicolas Lassauque; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-08       Impact factor: 15.336

7.  Bio-inspired NHC-organocatalyzed Stetter reaction in aqueous conditions.

Authors:  Mégane Debiais; Aladin Hamoud; Reihana Drain; Philippe Barthélémy; Valérie Desvergnes
Journal:  RSC Adv       Date:  2020-11-09       Impact factor: 4.036

Review 8.  Advancements in the mechanistic understanding of the copper-catalyzed azide-alkyne cycloaddition.

Authors:  Regina Berg; Bernd F Straub
Journal:  Beilstein J Org Chem       Date:  2013-12-02       Impact factor: 2.883

9.  Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors.

Authors:  Morgan Hans; Jan Lorkowski; Albert Demonceau; Lionel Delaude
Journal:  Beilstein J Org Chem       Date:  2015-11-25       Impact factor: 2.883

10.  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
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