Tuning and Quantifying Steric and Electronic Effects of N-Heterocyclic Carbenes

Laura Falivene, Albert Poater, Luigi Cavallo

Research output: Chapter in Book/Report/Conference proceedingChapter

5 Scopus citations


This chapter states that the main handles for tuning steric and electronic effects are the substituents on N atoms, the nature of the C4-C5 bridge (either saturated or unsaturated), and the substituents on the C4 and C5 atoms. The initial intuition that steric properties of N-heterocyclic carbenes (NHCs) could be modulated and could impact catalytic behavior stimulated the development of steric descriptors to quantify the steric requirement of different NHCs and, possibly, to compare them with tertiary phosphines. NHCs can be classified as typically strong σ-basic/π-acid ligands, although they have been also shown to exhibit reasonable π-basic properties. This electronic modularity allows NHC ligands to adapt flexibly to different chemical environments represented by a transition metal and the other ligands. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA. All rights reserved.
Original languageEnglish (US)
Title of host publicationN-Heterocyclic Carbenes
Number of pages14
ISBN (Print)9783527671229; 9783527334902
StatePublished - Jul 12 2014

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01


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