NMR, FTIR, ESI-MS and semiempirical study of a new 2-(2-hydroxyethoxy)ethyl ester of monensin A and its complexes with alkali metal cations

A new 2-(2-hydroxyethoxy)ethyl ester of monensin A (MON6) has been synthesized and its ability to form complexes with Li+, Na+ and K+ cations has been studied by ESI-MS, 1H and 13C NMR, FTIR, and PM5 semiempirical methods. It is demonstrated that MON6 has been able to form stable complexes of 1:1 stoichiometry with monovalent metal cations. The structures of the complexes are stabilized by intramolecular hydrogen bonds in which the OH groups are always involved. In the structure of MON6 the oxygen atom of the Cdouble bond; length as m-dashO ester group is involved in very weak bifurcated intramolecular hydrogen bonds with two hydroxyl groups whereas in the complexes of MON6 with monovalent metal cations the Cdouble bond; length as m-dashO ester group is not engaged in any intramolecular hydrogen bonds. The structures of the MON6 and its complexes with Li+, Na+ and K+ cations are visualized.