Sunghwan Kim - A theoretical investigation into the conformational changes of dibenzo-p-dioxin, thianthrene, and selenanthrene

Version 2

      Publication Details (including relevant citation   information):

      S. Kim, Y. Kwon,    J.-P. Lee, S.-Y. Choi, and J. Choo;

      Journal of Molecular Structure,   2003655, 451.



      Theoretical ab initio calculations using the HF and B3LYP methods   have been carried out to investigate the conformational   differences of three cyclic rings, dibenzo-p-dioxin (DPD),   thianthrene (THT), and selenanthrene (SET). The physical origin   for the conformational preference of each molecule has been   studied using the natural bond orbital (NBO) analysis. The NBO   results indicate that DPD exists in a planar form due to strong   electron delocalization caused by the specific orbital   interaction, nπ → π*CC, around the X atom. On the other hand, THT   and SET exist as puckered forms with high inversion barriers due   to less effective electron delocalization. The NBO analysis also   shows that the conformational stabilization in DPD is caused by a   more effective overlap of the 2Pz - π*CC orbitals, compared with   the overlap of the 3Pz - π*CC orbitals in THT.


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