Polarimetry was used to investigate the binding abilities of a chiral calix[4]resorcinarene derivative, bearing L-proline subunits, towards a set of suitably selected organic guests. The simultaneous formation of 1:1 and 2:1 host-guest inclusion complexes was observed in several cases, depending on both the charge status of the host and the structure of the guest. Thus, the use of the polarimetric method was thoroughly revisited, in order to keep into account the occurrence of multiple equilibria. Our data indicate that the stability of the host-guest complexes is affected by an interplay between Coulomb interactions, π-π interactions, desolvation effects and entropy-unfavorable conformational dynamic restraints. Polarimetry is confirmed as a very useful and versatile tool for the investigation of supramolecular interactions with chiral hosts, even in complex systems involving multiple equilibria.

Russo, M., & Lo Meo, P. (2017). Binding abilities of a chiral calix[4] resorcinarene: a polarimetric investigation on a complex case of study. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 13, 2698-2709 [10.3762/bjoc.13.268].

Binding abilities of a chiral calix[4] resorcinarene: a polarimetric investigation on a complex case of study

Russo, Marco;Lo Meo, Paolo
2017

Abstract

Polarimetry was used to investigate the binding abilities of a chiral calix[4]resorcinarene derivative, bearing L-proline subunits, towards a set of suitably selected organic guests. The simultaneous formation of 1:1 and 2:1 host-guest inclusion complexes was observed in several cases, depending on both the charge status of the host and the structure of the guest. Thus, the use of the polarimetric method was thoroughly revisited, in order to keep into account the occurrence of multiple equilibria. Our data indicate that the stability of the host-guest complexes is affected by an interplay between Coulomb interactions, π-π interactions, desolvation effects and entropy-unfavorable conformational dynamic restraints. Polarimetry is confirmed as a very useful and versatile tool for the investigation of supramolecular interactions with chiral hosts, even in complex systems involving multiple equilibria.
Settore CHIM/06 - Chimica Organica
Russo, M., & Lo Meo, P. (2017). Binding abilities of a chiral calix[4] resorcinarene: a polarimetric investigation on a complex case of study. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 13, 2698-2709 [10.3762/bjoc.13.268].
File in questo prodotto:
File Dimensione Formato  
2017 BJOC calix.pdf

accesso aperto

Dimensione 815.32 kB
Formato Adobe PDF
815.32 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10447/252601
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 7
  • ???jsp.display-item.citation.isi??? 8
social impact