Use of Charge-Charge Repulsion to Enhance π-Electron Delocalization into Anti-Aromatic and Aromatic Systems.
Chemistry
; 23(11): 2566-2570, 2017 Feb 21.
Article
em En
| MEDLINE
| ID: mdl-28072909
ABSTRACT
A series of 9-fluorenyl cations has been studied and it is shown that increasing charge on a heterocyclic substituent group enhances the anti-aromatic character of the carbocation system. Similarly, a series of dibenzosuberenyl cations has been studied and increasing charge on a substituent group is shown to enhance aromatic character in the carbocation system. These studies include the direct observations of dicationic and tricationic species using stable-ion conditions and low temperature NMR. The structures of these ions were further characterized using DFT calculations, confirming that highly charged organic ions may exhibit unusual distributions of π-electrons and delocalization of electrons in 4n or 4n+2 π-systems.
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2017
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Article