Topological transformation of a trefoil knot into a [2]catenane.
Fiche publication
Date publication
décembre 2017
Journal
Dalton transactions (Cambridge, England : 2003)
Auteurs
Membres identifiés du Cancéropôle Est :
Dr CHARBONNIERE Loïc, Dr ELHABIRI Mourad
Tous les auteurs :
Prakasam T, Bilbeisi RA, El-Khoury R, Charbonnière LJ, Elhabiri M, Esposito G, Olsen JC, Trabolsi A
Lien Pubmed
Résumé
Topological transformation of a zinc-templated trefoil knot, Zn-TK, into a zinc-templated [2]catenane, Zn-[2]C, was studied. The net reaction 2 Zn-TK→3 Zn-[2]C was accomplished in 89% yield by heating a solution of Zn-TK in DO. Kinetic investigation by H NMR spectroscopy and high resolution mass spectrometry revealed that the mechanism is complex, involving a large pool of intermediates that form after imine bond cleavage. Bromide ions, which can occupy the central cavity of Zn-TK, inhibited the reaction. Two similar transformations were also studied, one of a cadmium-containing trefoil knot, Cd-TK, into a cadmium-containing catenane, Cd-[2]C, and the other of Cd-TK into Zn-[2]C. The latter transformation could be achieved in one step at high temperature or in two steps via transmetallation to form Zn-TK at room temperature followed by topological conversion of Zn-TK to Zn-[2]C at high temperature.
Référence
Dalton Trans. 2017 Dec 21;46(47):16474-16479