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Title: Complexes of peracetylated cyclodextrin in a non-aqueous aprotic medium: the role of residual water
Authors: Jicsinszky, Laszlo
Martina, Katia
Caporaso, Marina
Cintas Moreno, Pedro
Zanichelli, Andrea
Cravotto, Giancarlo
Keywords: Ésteres aromáticos;Ciclodestrinas;Peracetilado;Espectroscopia de RMN;Aromatic esters;Cyclodextrins;Peracetylated;NMR spectroscopy
Issue Date: 2015
Publisher: Royal Society of Chemistry
Abstract: This paper describes the interaction between aromatic esters and peracetylated cyclodextrins (CDs) studied by NMR spectroscopy in deuterochloroform (CDCl3). The observed chemical shift changes highlight the existence of interactions between an aromatic alkyl ester, water and peracetylated CDs. In some cases, substituent chemical shift determination was influenced by the low water content of CDCl3 and/or the host molecule. Higher CD concentrations resulted in water signal drifts in all studied cases. It was not possible to obtain a completely dry sample of peracetyl γCD: ∼1 mol of water remained and the water signal showed reversed movement, with respect to the other two CD analogues, upon increasing host concentration. The estimated 1 : 1 stability constants for the water : peracetyl CD complexes are in the 50–150 M−1 range in CDCl3, but show a relatively large calculation error. The calculated 1 : 1 stability constants for the peracetyl CD : ester complexes are also in this range, but 1 : 2 and 2 : 1 complex compositions are also possible. Overall, our results highlight dynamic aspects of water nanoconfined in a highly hydrophobic environment, thus mimicking biological recognition where a few water molecules often play a pivotal role.
ISSN: 1463-9076
DOI: 10.1039/C5CP02379C
Appears in Collections:DQOIN - Artículos

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