Increased Halide Recognition Strength by Enhanced Intercomponent Preorganisation in Triazolium Containing [2] Rotaxanes
authors White, NG; Costa, PJ; Carvalho, S; Felix, V; Beer, PD
nationality International
journal CHEMISTRY-A EUROPEAN JOURNAL
author keywords anions; molecular dynamics; preorganisation; rotaxanes; triazolium
keywords ANION RECOGNITION; HYDROGEN-BONDS; MACROCYCLIC RECEPTOR; COMPUTER-PROGRAM; TERMINAL ALKYNES; AQUEOUS-MEDIA; ARYL-TRIAZOLE; BINDING; CHLORIDE; COMPLEXES
abstract Three triazolium-based [2]rotaxanes containing different sized axle and macrocycle components were synthesised in good yields (40-57%) through chloride anion templation. The anion recognition properties of the interlocked receptor systems were investigated using (HNMR)-H-1 titration experiments: all three rotaxanes display impressive selectivities for halide anions over the more basic oxoanion acetate. The rotaxanes incorporating shorter, more rigid axle components with aryl-substituted triazolium groups display substantially higher anion binding affinities than those with longer, bis-alkyl-substituted heterocycles, which is attributed to the increased intercomponent preorganisation afforded by the smaller axle component. Computational DFT and molecular dynamics simulations composed of unconstrained and umbrella sampling simulations corroborate the experimental observations.
publisher WILEY-V C H VERLAG GMBH
issn 0947-6539
year published 2013
volume 19
issue 52
beginning page 17751
ending page 17765
digital object identifier (doi) 10.1002/chem.201303122
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000328531000018
  ciceco authors
  impact metrics
journal analysis (jcr 2019):
journal impact factor 4.857
5 year journal impact factor 4.636
category normalized journal impact factor percentile 75.424
dimensions (citation analysis):
altmetrics (social interaction):



 


Apoio

1suponsers_list_ciceco.jpg