Quantification of the (anti)aromaticity of fulvalenes subjected to pi-electron cross-delocalization.
Fulvalenes 3-12 were theoretically studied at the ab initio level of theory. For the global minima structures, the occupation of the bonding (pi)C=C orbital of the interring C=C double bond obtained by NBO analysis quantitatively proves pi-electron cross-delocalization resulting in, at least partially, 2- or 6pi-electron aromaticity and 8pi-electron antiaromaticity for appropriate moieties. The cross-conjugation was quantified by the corresponding occupation numbers and lengths of the interring C=C double bonds, while the aromaticity or antiaromaticity due to cross-delocalization of the pi-electrons was visualized and quantified by through-space NMR shielding surfaces.
Kleinpeter
Erich
E
Chemisches Institut, Universität Potsdam, Karl-Liebknecht-Strasse 24-25, 14476 Golm, Germany.
Holzberger
Anja
A
Wacker
Philipp
P
D003198:Computer Simulation; D004583:Electrons; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory; D012015:Reference Standards
D006841:Hydrocarbons, Aromatic