Title :

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

Author(s) :

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

Journal title :

International Journal of Molecular Sciences

Volume number :

23

Publication date :

2022

HAL domain(s) :

Planète et Univers [physics]/Sciences de la Terre

English abstract : [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 ...
Show more >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.Show less >

Audience :

Non spécifiée

Popular science :

Non

Administrative institution(s) :

ENSCL
CNRS
Université de Lille

Collections :

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

Research team(s) :

Propriétés magnéto structurales des matériaux (PMSM)

Submission date :

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