1. Synthesis, FT-IR, ¹H, ¹³CNMR, ESI MS and PM5 studies of a new Mannich base of polyether antibiotic - Lasalocid acid and its complexes with Li⁺, Na⁺ and K⁺ cations.
- Author
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Huczyński A, Rutkowski J, Brzezinski B, and Bartl F
- Subjects
- Anti-Bacterial Agents chemistry, Carbon Isotopes, Hydrogen Bonding, Lasalocid chemistry, Lithium chemistry, Magnetic Resonance Spectroscopy, Mannich Bases chemical synthesis, Potassium chemistry, Protons, Sodium chemistry, Spectroscopy, Fourier Transform Infrared, Anti-Bacterial Agents chemical synthesis, Cations chemistry, Ethers chemistry, Lasalocid chemical synthesis, Mannich Bases chemistry, Models, Chemical, Spectrometry, Mass, Electrospray Ionization
- Abstract
The polyether antibiotic Lasalocid acid has been converted to its Mannich base derivative by a chemoselective one-pot reaction with formaldehyde and morpholine through the decarboxylation process. Spectroscopic studies of the structure of this new derivative have shown that in this ortho-phenol Mannich base the O-H⋯N intarmolecular hydrogen bond is present. The compound forms complexes with Li(+), Na(+) and K(+) cations of exclusively 1:1 stoichiometry. The structures of these complexes have been studied and visualized by semi-empirical calculation based on results of spectrometric and spectroscopic investigation. It is demonstrated that in contrast to Lasalocid acid the novel Mannich type derivative forms preferential complexes with Li(+) cation., (Copyright © 2012 Elsevier B.V. All rights reserved.)
- Published
- 2013
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