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Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4765-4768. doi: 10.1002/anie.201801596. Epub 2018 Mar 15.

Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes.

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Anorganische Molekülchemie und Katalyse, Lehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien, Fakultät für Chemie, Universität Bielefeld, Universitätsstrasse 25, 33615, Bielefeld, Germany.
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Mülheim an der Ruhr, Germany.
Allgemeine und Anorganische Chemie, Universität des Saarlandes, Campus C4.1, 66123, Saarbrücken, Germany.


One-electron reduction of C2-arylated 1,3-imidazoli(ni)um salts (IPrAr )Br (Ar=Ph, 3 a; 4-DMP, 3 b; 4-DMP=4-Me2 NC6 H4 ) and (SIPrAr )I (Ar=Ph, 4 a; 4-Tol, 4 b) derived from classical NHCs (IPr=:C{N(2,6-iPr2 C6 H3 )}2 CHCH, 1; SIPr=:C{N(2,6-iPr2 C6 H3 )}2 CH2 CH2 , 2) gave radicals [(IPrAr )]. (Ar=Ph, 5 a; 4-DMP, 5 b) and [(SIPrAr )]. (Ar=Ph, 6 a; 4-Tol, 6 b). Each of 5 a,b and 6 a,b exhibited a doublet EPR signal, a characteristic of monoradical species. The first solid-state characterization of NHC-derived carbon-centered radicals 6 a,b by single-crystal X-ray diffraction is reported. DFT calculations indicate that the unpaired electron is mainly located at the original carbene carbon atom and stabilized by partial delocalization over the adjacent aryl group.


EPR spectroscopy; N-heterocyclic carbenes; X-ray diffraction; density functional calculations; radicals


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