Unusual attractive interactions between selenium and oxygen in selenoiminoquinones Academic Article uri icon


  • The reaction of benzeneseleninic anhydride and hexamethyldisilazane gives a reactive intermediate namely oligomeric (RSeN)4 which oxidizes a phenol to the selenoiminoquinone 1. Both spectroscopic and crystallographic studies showed that the oxygen atom of the carbonyl group in the (phenylselenoimino)quinone 2 is involved in an attractive interaction with the selenium atom. The carbon atom of the phenyl ring is also found to be in the same plane as the O-C-C-N-Se plane. Theoretical studies of these systems clearly show a strong dependence of the Se-O interactions on the substituent on the selenium atom. The electronic structure around the selenium atom can be described in terms of the VSEPR model with a 3-center, 4-electron O-Se-R bond and correlated with other hypervalent molecules. © 1993, American Chemical Society. All rights reserved.

published proceedings

  • Journal of the American Chemical Society

author list (cited authors)

  • Barton, D., Hall, M. B., Lin, Z., Parekh, S. I., & Reibenspies, J

citation count

  • 93

complete list of authors

  • Barton, Derek HR||Hall, Michael B||Lin, Zhenyang||Parekh, Shyamal I||Reibenspies, Joseph

publication date

  • June 1993