title: Multinuclear magnetic resonance, electrospray ionization-mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2-thiophenecarbohydrazide as well as its complexes with LI+, Na+, K+, RB+, and Cs+ cations.
abstract: A new derivative of racemic gossypol with 2-thiophenecarbohydrazide (GHHT) and its complexes with monovalent cations have been synthesized and studied by electrospray ionization-mass spectroscopy (ESI-MS), multinuclear nuclear magnetic resonance (NMR), as well as by the Parametric Method 5 (PM5) methods. It is demonstrated that GHHT forms stable complexes of 1:1 stoichiometry with monovalent metal cations. The structures of the complexes are stabilized by three types of intramolecular hydrogen bonds. The spectroscopic methods have provided clear evidence that GHHT and its complexes exist in the DMSO-d6 solution in the N-imine-N-imine tautomeric forms. The structures of the GHHT and its complexes with Li+, Na+, K+, Rb+, and Cs+ cations are visualized and discussed in detail.
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland.
authors.forename: Piotr
authors.initials: P
authors.lastname: Przybylski
authors.forename: Wojciech
authors.initials: W
authors.lastname: Schilf
authors.forename: Weronika
authors.initials: W
authors.lastname: Lewandowska
authors.forename: Bogumil
authors.initials: B
authors.lastname: Brzezinski
mesh_terms: D002414:Cations, Monovalent / Q000737:chemistry*; D002586:Cesium / Q000737:chemistry; D004121:Dimethyl Sulfoxide; D006072:Gossypol / Q000031:analogs & derivatives* / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry; D007536:Isomerism; D008094:Lithium / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry; D015394:Molecular Structure; D011188:Potassium / Q000737:chemistry; D012964:Sodium / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013876:Thiophenes / Q000737:chemistry
chemical_list: D002414:Cations, Monovalent; D006834:Hydrazines; D008670:Metals; D013876:Thiophenes; D002586:Cesium; D008094:Lithium; D012964:Sodium; D006072:Gossypol; D011188:Potassium; C019289:carbohydrazide; D004121:Dimethyl Sulfoxide