Crown ether ditopic receptors for ammonium salts with high affinity for amino acid ester salts

Sharon Rosete-Luna, Felipe Medrano, Margarita I. Bernal-Uruchurtu, Carolina Godoy-Alcántar

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

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.
Original languageAmerican English
Pages (from-to)209-219
Number of pages11
JournalJournal of the Mexican Chemical Society
Volume53
Issue number4
StatePublished - 1 Oct 2009
Externally publishedYes

Keywords

  • Alkyl ammonium
  • Amino acid
  • Binding constant; Crown ethers
  • Ditopic receptors

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