title: Spectroscopic, mass spectrometry, and semiempirical investigation of a new ester of Monensin A with ethylene glycol and its complexes with monovalent metal cations.
abstract: A new ester of Monensin A with ethylene glycol (MON2) has been synthesized by a new method and its ability to form complexes with Li+, Na+, and K+ cations has been studied by ESI MS, 1H and 13C NMR, FT-IR, and PM5 semiempirical methods. It is demonstrated that MON2 forms 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 MON2 the oxygen atom of the C=O ester group is involved in very weak bifurcated intramolecular hydrogen bonds with two hydroxyl groups, whereas in the complexes of MON2 with monovalent metal cations the C=O ester group is not engaged in any intramolecular hydrogen bonds. The structures of the MON2 and its complexes with Li+, Na+, and K+ cations are visualized and discussed in detail.
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland.
authors.forename: Adam
authors.initials: A
authors.lastname: Huczyński
authors.forename: Piotr
authors.initials: P
authors.lastname: Przybylski
authors.forename: Bogumil
authors.initials: B
authors.lastname: Brzezinski
authors.forename: Franz
authors.initials: F
authors.lastname: Bartl
mesh_terms: D002414:Cations, Monovalent / Q000737:chemistry*; D004952:Esters; D019855:Ethylene Glycol / Q000737:chemistry*; D006860:Hydrogen Bonding; D008094:Lithium / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D013058:Mass Spectrometry / Q000379:methods*; D008958:Models, Molecular; D015394:Molecular Structure; D008985:Monensin / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry; D012964:Sodium / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D013816:Thermodynamics
chemical_list: D002414:Cations, Monovalent; D004952:Esters; D008985:Monensin; D008094:Lithium; D012964:Sodium; D019855:Ethylene Glycol; D011188:Potassium