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

Spectrochim Acta A Mol Biomol Spectrosc. 2013 Mar:104:497-504. doi: 10.1016/j.saa.2012.11.106. Epub 2012 Dec 8.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Carbon Isotopes
  • Cations / chemistry*
  • Ethers / chemistry*
  • Hydrogen Bonding
  • Lasalocid / chemical synthesis*
  • Lasalocid / chemistry
  • Lithium / chemistry
  • Magnetic Resonance Spectroscopy
  • Mannich Bases / chemical synthesis
  • Mannich Bases / chemistry*
  • Models, Chemical*
  • Potassium / chemistry
  • Protons
  • Sodium / chemistry
  • Spectrometry, Mass, Electrospray Ionization*
  • Spectroscopy, Fourier Transform Infrared


  • Anti-Bacterial Agents
  • Carbon Isotopes
  • Cations
  • Ethers
  • Mannich Bases
  • Protons
  • Lithium
  • Sodium
  • Potassium
  • Lasalocid