Quantifying and understanding the electronic properties of N-heterocyclic carbenes

David J. Nelson, Steven P. Nolan

Research output: Contribution to journalArticle

500 Citations (Scopus)

Abstract

The use of N-heterocyclic carbenes (NHCs) in chemistry has developed rapidly over the past twenty years. These interesting compounds are predominantly employed in organometallic chemistry as ligands for various metal centres, and as organocatalysts able to mediate an exciting range of reactions. However, the sheer number of NHCs known in the literature can make the appropriate choice of NHC for a given application difficult. A number of metrics have been explored that allow the electronic properties of NHCs to be quantified and compared. In this review, we discuss these various metrics and what they can teach about the electronic properties of NHCs. Data for approximately three hundred NHCs are presented, obtained from a detailed survey of the literature. 

LanguageEnglish
Pages6723-6753
Number of pages31
JournalChemical Society Reviews
Volume42
Issue number16
DOIs
Publication statusPublished - 21 Aug 2013
Externally publishedYes

Fingerprint

Electronic properties
Organometallics
carbene
Metals
Ligands

Keywords

  • N-heterocyclic carbenes
  • NHCs
  • electrochemistry
  • organometallic chemistry
  • organocatalysts

Cite this

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Quantifying and understanding the electronic properties of N-heterocyclic carbenes. / Nelson, David J.; Nolan, Steven P.

In: Chemical Society Reviews , Vol. 42, No. 16, 21.08.2013, p. 6723-6753.

Research output: Contribution to journalArticle

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