Electron Density of Aromatic Rings - Effect of Substituents
Tetracyanoethylene in dichloromethane is added to nitrobenzene, chlorobenzene, benzene, and anisole. The colors of the resulting products are compared. The 3 thumbnail images summarize the content of the video. Click an image to see the image gallery.
The intensity of the colors of complexes between benzene derivatives and tetracyanoethylene reveals their electron density.
A 1% solution of tetracyanoethylene (TCNE) in dichloromethane is added to each of four test tubes containing nitrobenzene, chlorobenzene, benzene, and anisole respectively. TCNE forms colored p-complexes with aromatic rings and the intensity of the color increasing with increasing electron density of the ring. The nitro- and chloro- groups are both electron withdrawing. Nitrobenzene gives no added color, and chlorobenzene gives a pale yellow color with TCNE. The methoxy group is strongly electron donating and gives a purple color with TCNE.
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