N-heterocyclic carbenes and parent cations: acidity, nucleophilicity, stability, and hydrogen bonding-Electrochemical Study and ab initio calculations

Renato Noto, Francesca D'Anna, Fabrizio Gala, Achille Inesi, Luigi Ornano, Isabella Chiarotto, Giuseppe Zollo, Marta Feroci

Risultato della ricerca: Article

12 Citazioni (Scopus)

Abstract

N-Heterocyclic carbenes (NHCs) are widely used as organocatalysts.Their reactivity (and instability) is related to their basicityand nucleophilicity, which, in turn, are linked to their scaffold.NHCs can be generated by chemical deprotonation or electrochemicalreduction of the parent azolium cations, NHCH+s.Cyclic voltammetry enabled the reduction potential of theNHCH+s to be determined; the reduction potential is relatedto the acidity of the NHCH+s and the oxidation potential ofthe NHCs, which is related to the nucleophilicity of the NHCs.It was thus possible to order different NHCH+s and NHCs bytheir acidity and nucleophilicity, respectively. A study on thestability of NHCs was also performed in the absence and in thepresence of acetic acid to assess the possibility of the coexistenceof NHC and an acid in the same solution, opening thepossibility of co-catalysis. Finally, ab initio calculations confirmedthe presence, in DMF, of hydrogen-bonded NHCH+–NHC adducts, which could influence catalyst activity.
Lingua originaleEnglish
pagine (da-a)1133-1141
Numero di pagine9
RivistaChemElectroChem
Volume3
Stato di pubblicazionePublished - 2016

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electrochemistry

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