Stabilization of unsymmetrically annelated imidazol-2-ylidenes with respect to their higher group 14 homologues by n-/π-HOMO inversion

Farman Ullah, Gabor Bajor, T. Veszprémi, Peter G. Jones, Joachim W. Heinicke

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

(Chemical Equation Presented) From annelation to an elation: The surprising stability of pyridoannelated imidazol-2-ylidenes (see scheme) in comparison with the heavier Group 14 homologues suggests broad tuning potential and control of the reactivity by the lone pair of electrons at the carbon atom. The asymmetric distribution of π-electron density, which destabilizes the heavier homologues, does not markedly diminish the kinetic stability of the N-heterocyclic carbenes (NHCs).

Original languageEnglish
Pages (from-to)2697-2700
Number of pages4
JournalAngewandte Chemie - International Edition
Volume46
Issue number15
DOIs
Publication statusPublished - 2007

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Stabilization
Carrier concentration
Carbon
Tuning
Atoms
Kinetics
Electrons
carbene

Keywords

  • Carbenes
  • Electronic structure
  • Imidazolium
  • Photoelectron spectroscopy
  • Silylenes

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Stabilization of unsymmetrically annelated imidazol-2-ylidenes with respect to their higher group 14 homologues by n-/π-HOMO inversion. / Ullah, Farman; Bajor, Gabor; Veszprémi, T.; Jones, Peter G.; Heinicke, Joachim W.

In: Angewandte Chemie - International Edition, Vol. 46, No. 15, 2007, p. 2697-2700.

Research output: Contribution to journalArticle

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