Comment on “Synthesis, Characterization, and Structures of Persistent Aniline Radical Cation”: It Is a Protonated Aniline and Not an Aniline Radical Cation


  • We thank the National Science Foundation for financial support and Qadir K. Timerghazin for helpful discussions. The calculations were performed on the high-performance computing cluster Père at Marquette University funded by NSF awards OCI-0923037 and CBET-0521602.


original image

The same, but different: The reaction of tri-tert-butylaniline (TBA) with AgSbF6 in CH2Cl2 produces a green-colored intermediate which undergoes decomposition to form a protonated aniline (TBAH+SbF6). Crystals of the protonated aniline salt (see picture) were analyzed by X-ray diffraction and found to have the same crystal characteristics as the crystals of the supposed cation radical first identified in 2012.