[2]pseudorotaxane formation with N-benzylanilinium axles and 24-crown-8 ether wheels

Stephen J Loeb; Jorge Tiburcio; Sarah J Vella

doi:10.1021/ol051786e

[2]pseudorotaxane formation with N-benzylanilinium axles and 24-crown-8 ether wheels

Org Lett. 2005 Oct 27;7(22):4923-6. doi: 10.1021/ol051786e.

Authors

Stephen J Loeb¹, Jorge Tiburcio, Sarah J Vella

Affiliation

¹ Department of Chemistry & Biochemistry, University of Windsor, ON, Canada. loeb@uwindsor.ca

PMID: 16235923
DOI: 10.1021/ol051786e

Abstract

[reaction: see text] As a hybrid of the N,N-dibenzylammonium and 1,2-bis(pyridinium)ethane axles, various N-benzylanilinium cations were investigated as suitable axles for the formation of [2]pseudorotaxanes with the 24-membered crown ethers 24C8 and DB24C8. The effect of electron-donating OCH(3) and electron-withdrawing CF(3) groups on both the anilinium and benzyl aromatic rings was studied. Formation constants and structural details were compared to the [2]pseudorotaxanes formed by the two aforementioned dibenzylammonium and 1,2-bis(pyridinium)ethane axles.