Abstract
Binding in phenonium ions [C6H5−C2(OH)4]+, [C6H5−C2(CH3)4]+, [C6H5−C2F4]+, [p-NC−C6H4−C2H4]+, [p-OHC−C6H4−C2H4]+, [C6H5−C2H4]+, [p-F−C6H4−C2H4]+, [p-H3C−C6H4−C2H4]+, [p-HO−C6H4−C2H4]+, [C6H5−C2(CHO)4]+, and [C6H5−C2(CN)4]+ was investigated with the B3LYP/6-31G* method. The analysis of the Kohn−Sham orbitals and a Bader analysis of the computed electron density of the phenonium ion, [C6H5−C2H4]+, clearly show that back-bonding from the phenyl cation moiety to the ethylene fragment determines the formation of the three-membered cycle, rendering the shielding of the ipso carbon atom similar to that for an sp3 C, while an extension of the conjugation occurs as both π systems merge with each other. The important stabilization gained from this process determines the orthogonal conformation of the phenonium ion.
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