Abstract
Density functional theory [DFT B3LYP/6-311++G(d,p)] simulation has revealed stable tautomers and conformers of polydentate ligand system based on 5,7-di(tert-butyl)-2-(8-hydroxyquinolin-2-yl)-1,3-tropolone with different structures of the coordination nodes, capable of formation of metal chelates. It has been shown that the tautomeric NH- and OH- forms with exo and endo location of the hydroxy group in the quinoline fragments (close in energy, ΔE ZPE = 0.2–2.4 kcal/mol) are stabilized by intramolecular hydrogen bonds. Energy barriers of the interconversion of these forms via rotation about the C–OH bond of the phenolic fragment are of ΔE ≠ZPE = 2.1–4.2 kcal/mol, whereas the barrier of rotation about the bond between the quinoline and tropolone fragments is higher (ΔE ≠ZPE = 18.2 and 19.6 kcal/mol).
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Original Russian Text © G.A. Dushenko, I.E. Mikhailov, Yu.M. Artyushkina, O.I. Mikhailova, V.V. Tkachev, S.M. Aldoshin, V.I. Minkin, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 6, pp. 976–983.
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Dushenko, G.A., Mikhailov, I.E., Artyushkina, Y.M. et al. Quantum-chemical simulation of structure and conformational flexibility of 5,7-di(tert-butyl)-2-(8-hydroxyquinolin-2-yl)-1,3-tropolone. Russ J Gen Chem 86, 1306–1313 (2016). https://doi.org/10.1134/S1070363216060141
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DOI: https://doi.org/10.1134/S1070363216060141