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Dications Of 3-Phenyl-Indenylidene Dibenzo[ A.D ]Cycloheptene: The Role Of Charge In The Antiaromaticity Of Cationic Systems, Nancy S. Mills, Francine E. Cheng, Joseph M. Baylan, Cornelia Tirla, Jennifer L. Hartmann, Kiran C. Patel, Bart J. Dahl, Sean P. Mcclintock

Chemistry Faculty Research

Dications of 9-(3-phenyl-1H-inden-1-ylidene)-5H-dibenzo[a,d]cycloheptene, 52+, were prepared by oxidation with SbF5 in SO2ClF, and their magnetic behavior was compared to dications of 9-(3-phenyl-1H-inden-1-ylidene)-9H-fluorene, 22+. The good correlation between the experimental 1H NMR shifts for the dications that were oxidized cleanly and the chemical shifts calculated by the GAIO method supported the use of the nucleus independent chemical shifts, NICS, to evaluate the antiaromaticity of the indenyl systems of 22+/52+ and their unsubstituted parent compounds, 62+ and 72+, as well as the antiaromaticity of the fluorenyl system of 22+/72+ …