Titre :

Chiral Discrimination Mechanisms by Silylated-Acetylated Cyclodextrins: Superficial Interactions vs. Inclusion

Auteur(s) :

Balzano, Federica [Auteur]
University of Pisa [Italy] = Università di Pisa [Italia] = Université de Pise [Italie] [UniPi]
Uccello-Barretta, Gloria [Auteur]
University of Pisa [Italy] = Università di Pisa [Italia] = Université de Pise [Italie] [UniPi]
Sicoli, Giuseppe [Auteur]
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement (LASIRE) - UMR 8516
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Vanni, Letizia [Auteur]
University of Pisa [Italy] = Università di Pisa [Italia] = Université de Pise [Italie] [UniPi]
Recchimurzo, Alessandra [Auteur]
University of Pisa [Italy] = Università di Pisa [Italia] = Université de Pise [Italie] [UniPi]
Aiello, Federica [Auteur]
CNR Istituto per i Processi Chimico-Fisici [IPCF]

Titre de la revue :

International Journal of Molecular Sciences

Numéro :

23

Date de publication :

2022

Discipline(s) HAL :

Planète et Univers [physics]/Sciences de la Terre

Résumé en anglais : [en]

Cyclodextrin derivatives constitute a powerful class of auxiliary agents for the discrimination of apolar chiral substrates. Both host-guest inclusion phenomena and interactions with the derivatizing groups located on the ...
Lire la suite >Cyclodextrin derivatives constitute a powerful class of auxiliary agents for the discrimination of apolar chiral substrates. Both host-guest inclusion phenomena and interactions with the derivatizing groups located on the surface of the macrocycle could drive the enantiodiscrimination; thus, it is important to understand the role that these processes play in the rational design of new chiral selectors. The purpose of this study is to compare via nuclear magnetic resonance (NMR) spectroscopy the efficiency of silylated-acetylated α-, β-, and γ-cyclodextrins in the chiral discrimination of 1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane (compound B) and methyl 2-chloropropionate (MCP). NMR DOSY (Diffusion Ordered SpectroscopY) experiments were conducted for the determination of the bound molar fractions and the association constants, whereas ROESY (Rotating-frame Overhauser Enhancement SpectroscopY) measurements provided information on the hosts' conformation and on the interaction phenomena with the guests. Compound B, endowed with fluorinated moieties, is not deeply included due to attractive Si-F interactions occurring at the external surface of the cyclodextrins. Therefore, a low selectivity toward the size of cyclodextrin cavity is found. By contrast, enantiodiscrimination of MCP relies on the optimal fitting between the size of the guest and that of the cyclodextrin cavity.Lire moins >

Audience :

Non spécifiée

Vulgarisation :

Non

Établissement(s) :

ENSCL
CNRS
Université de Lille

Collections :

• Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement (LASIRE) - UMR 8516

Équipe(s) de recherche :

Propriétés magnéto structurales des matériaux (PMSM)

Date de dépôt :

2024-02-21T17:11:56Z
2024-02-23T13:59:08Z