Physical Sciences and Mathematics Commons^™

Aromatic Ouroboroi: Heterocycles Involving A Sigma-Donor-Acceptor Bond And 4n+2 Pi-Electrons, Kelling J. Donald, William Tiznado, Rodrigo Baez-Grez, Diego Inostroza

Chemistry Faculty Publications

The aromaticity and dynamics of a set of recently proposed neutral 5- and 6-membered heterocycles that are closed by dative (donor–acceptor) or multi-center s bonds, and have resonance forms with a Hu¨ckel number of p-electrons, are examined. The donors and acceptors in the rings include N, O, and F, and B, Be, and Mg, respectively. The planar geometry of the rings, coupled with evidence from different measures of aromaticity, namely the NICSzz, and NICSpzz components of the conventional nucleus independent chemical shifts (NICS), and ring current strengths (RCS), indicate non-trivial degrees of aromaticity in certain cases, including the cyclic C3B2OH6 …