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)
%0 Journal Article
%1 Mondal.2014c
%A Mondal, Kartik Chandra
%A Samuel, Prinson P.
%A Roesky, Herbert W.
%A Niepoetter, Benedikt
%A Herbst-Irmer, Regine
%A Stalke, Dietmar
%A Ehret, Fabian
%A Kaim, Wolfgang
%A Maity, Bholanath
%A Koley, Debasis.
%D 2014
%J Chemistry - A European Journal
%K amino carbene crystal functionalized hexafluorophosphate;crystal mol monoradical monoradical;quinodimethane phenylation prepn reaction structure structure;trichlorosilyl triphenylcarbenium triphenylsilyl
%N 30
%P 9240--9245
%R 10.1002/chem.201400393
%T Synthesis and Characterization of a Triphenyl-Substituted Radical and an Unprecedented Formation of a Carbene-Functionalized Quinodimethane
%V 20
%X 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)
@article{Mondal.2014c,
abstract = {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)]},
added-at = {2019-07-15T13:41:23.000+0200},
author = {Mondal, Kartik Chandra and Samuel, Prinson P. and Roesky, Herbert W. and Niepoetter, Benedikt and Herbst-Irmer, Regine and Stalke, Dietmar and Ehret, Fabian and Kaim, Wolfgang and Maity, Bholanath and Koley, Debasis.},
biburl = {https://puma.ub.uni-stuttgart.de/bibtex/2a2dbe408bbb407002f9e8de9c86686bc/b_schwederski},
doi = {10.1002/chem.201400393},
interhash = {15fdc650a144007678197021e49d38f4},
intrahash = {a2dbe408bbb407002f9e8de9c86686bc},
issn = {0947-6539},
journal = {Chemistry - A European Journal},
keywords = {amino carbene crystal functionalized hexafluorophosphate;crystal mol monoradical monoradical;quinodimethane phenylation prepn reaction structure structure;trichlorosilyl triphenylcarbenium triphenylsilyl},
number = 30,
pages = {9240--9245},
timestamp = {2019-07-15T11:42:10.000+0200},
title = {Synthesis and Characterization of a Triphenyl-Substituted Radical and an Unprecedented Formation of a Carbene-Functionalized Quinodimethane},
volume = 20,
year = 2014
}
