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Journal of the Mexican Chemical Society

versión impresa ISSN 1870-249X

J. Mex. Chem. Soc vol.53 no.4 México oct./dic. 2009

 

Article

 

Crown Ether Ditopic Receptors for Ammonium Salts with High Affinity for Amino Acid Ester Salts

 

Sharon Rosete–Luna, Felipe Medrano, Margarita I. Bernal–Uruchurtu, and Carolina Godoy–Alcántar*

 

Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, 62209 Cuernavaca, Morelos, México. Tel/Fax: +52 777329 7997. *Responsible author: cga@uaem.mx

 

Received August 13, 2009
Accepted November 19, 2009

 

Abstract

Two bis crown ether receptors were synthesized and tested as host molecules for protonated forms of alkyl amines and amino acid esters. Molecular recognition studies were conducted in CH2Cl2:MeOH (92:8) by spectrophotometric UV/Vis titrations and by spectrometric 1H NMR titrations in CDCl3. The calculated binding constants are in the range 102–105 M–1. A high affinity for L–amino acid methyl ester derivatives was found. A theoretical study at the DFT level of the synthesized receptor and some analog ligands with three different ammonium ions helps to rationalize the experimentally found trends.

Key words: Ditopic Receptors, Binding Constant; Crown Ethers, Alkyl Ammonium, Amino Acid.

 

Resumen

En este trabajo se sinterizaron dos receptores del tipo bis eter corona y fueron estudiados como moléculas anfitrión de alquilaminas y ésteres de aminoácidos protonados. Se realizaron estudios de reconocimiento molecular por titulaciones espectrofotométricas UV/Vis en CH2Cl2:MeOH (92:8) y por titulaciones espectrométricas de RMN 1H en CDCl3. Las constantes de enlace calculadas están en el intervalo 102–105 M–1. Se encontró una alta afinidad por los ésteres metílicos de los L–aminoácidos estudiados. Un estudio teórico a nivel DFT de los receptores sinterizados y algunos ligandos análogos con tres diferentes iones amonio permite explicar las tendencias experimentales encontradas.

Palabras clave: Receptores ditópicos, constante de enlace, éteres corona, alquilamonio, aminoácido.

 

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Acknowledgements

We thank Professor A. K. Yatsimirsky for the advice and fruitful discussion of the results. SRL thanks CONACyT for the Ph. D. Fellowship. This work was supported by CONACyT, projects 39574-Q and 60747.

 

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