CHED 293 |
| Organic chemistry textbooks use benzene as the standard for aromaticity and require aromatic compounds to possess certain characteristics such as planarity and equal bond lengths around the ring. [14]Annulene is an interesting study in the possible deviation of annulenes from traditional behavior. Recent computational studies have, for example, revealed a configuration of [14]annulene possibly at an energy minimum with two half twists in the pi system (1). Computations were performed on 1 using both BHandHLYP and B3LYP methods. B3LYP calculations predict a bond equalized structure for 1, whereas BHandHLYP predicts a bond alternating geometry with a very small barrier to bond shifting. An attempt was also made to determine the mechanism for configuration change between 2 and 3 (Scheme 1) via planar non-degenerate bond shifting. Other mechanisms considered include bond shifting via twisted conformations such as 1.
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Undergraduate Research Poster Session: Organic Chemistry
2:30 PM-4:30 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Poster
Division of Chemical Education |
