Quinone-Annulated N-Heterocyclic Carbene−Transition-Metal Complexes: Observation of π-Backbonding Using FT-IR Spectroscopy and Cyclic Voltammetry

Citations Over TimeTop 10% of 2006 papers

Abstract

A new N-heterocyclic carbene architecture comprising a 1,4-naphthoquinone annulated to 1,3-dimesitylimidazolylidene (NpQ-NHC) was synthesized in two high yielding steps from commercially available starting materials. The free NpQ-NHC was characterized (solution and solid-state) and was used to synthesize various Rh and Ag complexes that ranged in pi-electron density. Enabled by the quinone moiety, the pi-systems of these complexes were analyzed using infrared spectroscopy and cyclic voltammetry. In contrast to previous reports, pi-backbonding was found to be non-negligible and was directly influenced by the metal's electronic character.

Related Papers

• → General and efficient synthesis of β-lactams bearing a quinone moiety at N1, C3 or C4 positions(2001)24 cited
• → The formation of dibenzofurans in acid-catalysed quinone–phenol reactions and quinone oligomerisations: evidence for quinone hemiacetal intermediates(1979)8 cited
• → A new natural quinone, 2-methyl-3-II,III,VIII-hexahydromultiprenyl9-1,4-naphthoquinone.(1980)3 cited
• → Mechanism of Antimicrobial Effect of Quinone Compounds(1962)