Bicycloaromaticity

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Bicycloaromaticity in chemistry is an extension of the concept of homoaromaticity with two aromatic ring currents situated in a non-planar molecule and sharing the same electrons.[1] The concept originates with Melvin Goldstein who first reported about it in 1967.[2][3][4] It is of some importance in academic research. Using MO theory the bicyclo[3.2.2]nonatrienyl cation was predicted to be destabilised and the corresponding anion predicted to be stabilised by bicycloaromaticity.

Bicycloaromaticity has been studied by others in relation to the bicyclo[3.2.2]nonatrienyl cation

bicyclic porphyrinoid.[1][8] This system has been described as aromatic with two ring systems of 26 (n=6) and 34 (n=8) electrons. By oxidation, another system was described as a triplet-state biradical, again considered aromatic by application of Baird's rule
.

References

  1. ^
    doi:10.1038/nchem.2834
  2. doi:10.1021/ja01000a069
  3. doi:10.1021/ja01000a068
  4. doi:10.1016/S0065-3160(08)60224-5
  5. doi:10.1021/ja00713a045
  6. doi:10.1021/ja00762a008
  7. doi:10.1021/ja00396a013
  8. ^ Unusual bicyclic molecule extends frontier of aromaticity Katrina Krämer Chemistry World 2017 link
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