Binding of Tetramethylammonium to Polyether Side-chained Aromatic Hosts. Evaluation of the Binding Contribution from Ether Oxygen Donors (Articolo in rivista)

Type
Label
  • Binding of Tetramethylammonium to Polyether Side-chained Aromatic Hosts. Evaluation of the Binding Contribution from Ether Oxygen Donors (Articolo in rivista) (literal)
Anno
  • 2003-01-01T00:00:00+01:00 (literal)
Alternative label
  • Bartoli S. 1, De Nicola G. 2, Roelens S. 3 (2003)
    Binding of Tetramethylammonium to Polyether Side-chained Aromatic Hosts. Evaluation of the Binding Contribution from Ether Oxygen Donors
    in Journal of organic chemistry
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Bartoli S. 1, De Nicola G. 2, Roelens S. 3 (literal)
Pagina inizio
  • 8149 (literal)
Pagina fine
  • 8156 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#altreInformazioni
  • Articolo su lavoro di ricerca di interesse nel campo del riconoscimento molecolare, pubblicato su rivista di prestigio dell' American Chemical Society ad elevato fattore d'impatto (IF: 3.217; fonte: ISI 2002) (literal)
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  • 68 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#descrizioneSinteticaDelProdotto
  • Pubblicazione scientifica. L'articolo descrive un'analisi dei contributi energetici dei gruppi funzionali al riconoscimento molecolare dell'acetilcolina da parte di recettori sintetici di tipo ciclofanico. E' stato chiarito il ruolo fondamentale dell'interazione di cationi organici come l'acetilcolina con anelli aromatici, che apportano un contributo al riconoscimento nettamente superiore a quello di leganti ben noti come i polieteri (eteri corona). (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • 3 CNR - ICCOM (Firenze) (literal)
Titolo
  • Binding of Tetramethylammonium to Polyether Side-chained Aromatic Hosts. Evaluation of the Binding Contribution from Ether Oxygen Donors (literal)
Abstract
  • A set of macrocyclic and open-chain aromatic ligands endowed with polyether side-chains has been prepared to assess the contribution of ether oxygen donors to the binding of tetramethylammonium (TMA), a cation believed incapable of interacting with oxygen donors. The open-chain hosts consisted of an aromatic binding site and side chains possessing a variable number of ether oxygen donors; the macrocyclic ligands were based on the structure of a previously investigated host, the dimeric cyclophane 1,4-xylylene-1,4-phenylene diacetate (DXPDA), implemented with polyether-type side chains in the backbone. Association to tetramethylammonium picrate (TMAP) was measured in CDCl3 at T = 296 K by 1H NMR titrations. Results confirm that the main contribution to the binding of TMA comes from the cation-p interaction established with the aromatic binding sites, but unequivocally show that polyether chains participate with cooperative contributions, although of markedly smaller entity. Water is also bound, but the two guests interact with aromatic rings and oxygen donors in an essentially noncompetitive way. An improved procedure for the preparation of cyclophanic tetraester derivatives has been developed, which conveniently recycles the oligomeric ester by-products formed in the one-pot cyclization reaction. An alternative entry to benzylic diketones has also been provided, which makes use of a low order cyanocuprate reagent to prepare in fair yields a class of compounds otherwise uneasily accessible. (literal)
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