Bingel-Hirsch addition on non-isolated-pentagon-rule Gd3N@C2n (2n = 82 and 84) metallofullerenes: products under kinetic control

J Org Chem. 2013 Oct 4;78(19):9986-90. doi: 10.1021/jo4014832. Epub 2013 Sep 16.

Abstract

Bingel-Hirsch reactions on fullerenes take place under kinetic control. We here predict, by means of DFT methodology, the products of the Bingel-Hirsch addition on non-isolated-pentagon-rule (non-IPR) metallofullerenes Gd3N@C2n (2n = 82, 84), as modeled by closed-shell Y3N@C2n systems. Adducts on [6,6] B-type bonds placed near the pentalene unit are predicted for the two cages, as found for other non-IPR endohedral fullerenes such as Sc3N@C68.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coordination Complexes / chemistry*
  • Fullerenes / chemistry*
  • Gadolinium / chemistry*
  • Isomerism
  • Kinetics
  • Molecular Structure

Substances

  • Coordination Complexes
  • Fullerenes
  • Gadolinium