Geometry‐based analysis of azulene and azulene‐like systems with H‐ or Li‐bonding |
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| Authors: | Tadeusz M. Krygowski Joanna E. Zachara‐Horeglad |
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| Affiliation: | 1. Faculty of Chemistry, Warsaw University, Pasteura 1, 02‐093 Warsaw, PolandFaculty of Chemistry, Warsaw University, Pasteura 1, 02‐093 Warsaw, Poland.===;2. Faculty of Chemistry, Warsaw University, Pasteura 1, 02‐093 Warsaw, Poland |
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| Abstract: | B3LYP/6–311+G** optimization was carried out for azulene and its analogs, in which CH? CH? CH fragment was replaced with O···X···O (X = H or Li). π‐electron delocalization in four possible derivatives with H‐bonding and three possible derivatives with Li‐bonding was described by the use of HOMA index. All derivatives with Li‐bonding exhibit high π‐electron delocalization similar to that found for azulene. Among four H‐bonded systems, two exhibit lower π‐electron delocalization (HOMA < 0.39) and higher total electron energy than the other two derivatives. Copyright © 2007 John Wiley & Sons, Ltd. |
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| Keywords: | azulene π ‐electron delocalization aromaticity H‐bonding Li‐bonding |
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