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Full-Text Articles in Physical Sciences and Mathematics
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
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+ …
Dications Of Benzylidenefluorene And Diphenylmethylidene Fluorene: The Relationship Between Magnetic And Energetic Measures Of Antiaromaticity, Catherine Do, Julianne Hatfield, Shirali Patel, D Vasudevan, Cornelia Tirla, Nancy S. Mills
Dications Of Benzylidenefluorene And Diphenylmethylidene Fluorene: The Relationship Between Magnetic And Energetic Measures Of Antiaromaticity, Catherine Do, Julianne Hatfield, Shirali Patel, D Vasudevan, Cornelia Tirla, Nancy S. Mills
Chemistry Faculty Research
Oxidation of m- and p-substituted benzylidene fluorenes to antiaromatic dications was attempted by electrochemical and chemical means. Electrochemical oxidation to dications was successful for benzylidene fluorenes with p-methoxy, p-methyl, p-fluoro, and unsubstituted phenyl rings in the 3-position; attempts to oxidize the m-substituted derivatives via electrochemistry were unsuccessful. Chemical oxidation with SbF5/SO2ClF gave the dication of 9-[(4-methoxyphenyl)methylene]-9H-fluorene cleanly; oxidation of all other substituted benzylidene fluorenes resulted in mixtures of products. The excellent linear relationship between the chemical shifts calculated by the GIAO method and the experimental shifts for the p-methoxy-substituted benzylidene fluorene dication …