Abstract
Salts containing aniline radical cations have been isolated and characterized by electron paramagnetic resonance (EPR) spectroscopy, UV-Vis absorption spectroscopy and single crystal X-ray diffraction. The EPR spectra and theoretical calculations indicate the unpaired electron is delocalized on phenyl rings and nitrogen atoms. Both radical cations feature a quinoidal geometry with a partially double C–N bond, but are distinct in that the C–N bond is coplanar to the phenyl plane in one cation while deviates from the plane in the other due to steric crowding. The work provides the first unequivocal examples of stable aniline radical cations.
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This work was supported by National Natural Science Foundation of China (21171087), and the Natural Science Foundation of Jiangsu Province (BK20140014).
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Zhang, S., Wang, W., Liu, S. et al. Putting aniline radical cations in a bottle. Sci. China Chem. 60, 1439–1443 (2017). https://doi.org/10.1007/s11426-017-9096-7
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DOI: https://doi.org/10.1007/s11426-017-9096-7