Chiral bis(amino amides) as chiral solvating agents for enantiomeric excess determination of α-hydroxy and arylpropionic acids
Impact
Scholar |
Other documents of the author: Altava, Belen; Burguete, M. Isabel; Carbó Mestre, Noèlia; Escorihuela, Jorge; Luis, Santiago V.
Metadata
Show full item recordcomunitat-uji-handle:10234/9
comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
comunitat-uji-handle4:
INVESTIGACIONThis resource is restricted
http://dx.doi.org/10.1016/j.tetasy.2010.05.010 |
Metadata
Title
Chiral bis(amino amides) as chiral solvating agents for enantiomeric excess determination of α-hydroxy and arylpropionic acidsAuthor (s)
Date
2010Publisher
ElsevierISSN
9574166Bibliographic citation
Tetrahedron Asymmetry, 21, 8, p. 982-989Type
info:eu-repo/semantics/articleAbstract
A family of bis(amino amides) derived from natural amino acids has been synthesized and tested for the NMR enantiodiscrimination, as chiral solvating agents, for enantiomeric excess determination of some carboxylic ... [+]
A family of bis(amino amides) derived from natural amino acids has been synthesized and tested for the NMR enantiodiscrimination, as chiral solvating agents, for enantiomeric excess determination of some carboxylic acids. Those bis(amino amide) receptors contain different structural modifications and the splitting of the signals of the acids, after addition of the corresponding CSAs, depends on those structural variables. The influence of aminoacid side chain and the nature of the aliphatic spacer are important parameters to obtain good chiral discriminations. The results obtained clearly show the chiral recognition abilities of these bis(amino amide) ligands and suggest their advantageous use as chiral solvating agents for carboxylic acids. The binding between bis(amino amides) and carboxylic acids has been studied by ESI-MS, NMR, DSC, and molecular modeling. The data suggest that enantiodiscrimination involves the formation of an ionic pair after proton transfer from the carboxylic substrate to the bis(amino amides). © 2010 Elsevier Ltd. All rights reserved. [-]
Rights
http://rightsstatements.org/vocab/CNE/1.0/
info:eu-repo/semantics/closedAccess
info:eu-repo/semantics/closedAccess
This item appears in the folowing collection(s)
- QUIO_Articles [705]