Synthesis and Characterization of a Triphenyl-Substituted Radical and an Unprecedented Formation of a Carbene-Functionalized Quinodimethane

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Chemistry - A European Journal, 20 (30): 9240--9245 (2014)
DOI: 10.1002/chem.201400393


The trichlorosilylcarbene monoradical (Cy-cAAC·)SiCl3 (1) was directly converted to (Cy-cAAC·)SiPh3 (2) by substitution of the three chlorine atoms with Ph groups without affecting the radical center adjacent to the silicon atom. In addn. to the structure detn., compd. 2 was studied by EPR spectroscopy and DFT calcns. The three hyperfine lines in the EPR spectrum of 2 are due to the coupling with 14N nucleus. Functionalized 1,4-quinodimethane Me2-cAAC:C6H4:CPh2 (7) was isolated, whereas carbon analog of radical 2 was targeted. Cyclic voltammogram of 7 indicated that a stable radical-anion 7·-, as well as a radical-cation 7·+, can be prepd. Theor. calcns. showed that one-electron ionization energy and electron affinity of 7 are 5.1 and 0.7 eV mol-1, resp. on SciFinder(R)



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