The Electronic Structure of Phenylene and Naphthylene Bicyclobutanes. Photoelectron spectroscopy and model calculations |
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Authors: | Rolf Gleiter,Klaus Gubernator,Mirjana Eckert-Maksi ,Jens Spanget-Larsen,Bernard Bianco,G rard Gandillon,Ulrich Burger |
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Affiliation: | Rolf Gleiter,Klaus Gubernator,Mirjana Eckert-Maksić,Jens Spanget-Larsen,Bernard Bianco,Gérard Gandillon,Ulrich Burger |
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Abstract: | The photoelectron (PE.) spectra of 1,2,3-methenoindane ( 2 ), 1,2,3-metheno-2,3-dihydro-1H-cyclopenta [b]naphthalene ( 3 ) and 1,2,3-metheno-2,3-dihydro-1H-phenalene ( 4 ) are investigated. The PE. spectrum of 1,3-methano-2,3-dihydrophenalene ( 7 ) is reported and compared with that of 4 . The experimental results are analyzed in terms of empirical correlation diagrams and the results of semiempirical MINDO/3 and CNDO/S calculations. The analysis indicates that the strong impact of the bicyclobutylene group on the spectroscopic properties of the aromatic π-systems in 2 , 3 and 4 is due to hyperconjugative interactions involving bicyclobutane Walsh orbitals. |
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