Quantum-chemical simulation of structure and conformational flexibility of 5,7-di(tert-butyl)-2-(8-hydroxyquinolin-2-yl)-1,3-tropolone
- Authors: Dushenko G.A.1, Mikhailov I.E.1,2, Artyushkina Y.M.1, Mikhailova O.I.1, Tkachev V.V.3, Aldoshin S.M.3, Minkin V.I.2
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Affiliations:
- Southern Scientific Center
- Scientific Research Institute of Physical and Organic Chemistry
- Institute of Problems of Chemical Physics
- Issue: Vol 86, No 6 (2016)
- Pages: 1306-1313
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/215269
- DOI: https://doi.org/10.1134/S1070363216060141
- ID: 215269
Cite item
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, ΔEZPE = 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 ΔEZPE≠ = 2.1–4.2 kcal/mol, whereas the barrier of rotation about the bond between the quinoline and tropolone fragments is higher (ΔEZPE≠ = 18.2 and 19.6 kcal/mol).
About the authors
G. A. Dushenko
Southern Scientific Center
Email: mikhail@ipoc.rsu.ru
Russian Federation, ul. Chekhova 41, Rostov-on-Don, 344006
I. E. Mikhailov
Southern Scientific Center; Scientific Research Institute of Physical and Organic Chemistry
Author for correspondence.
Email: mikhail@ipoc.rsu.ru
Russian Federation, ul. Chekhova 41, Rostov-on-Don, 344006; Rostov-on-Don
Yu. M. Artyushkina
Southern Scientific Center
Email: mikhail@ipoc.rsu.ru
Russian Federation, ul. Chekhova 41, Rostov-on-Don, 344006
O. I. Mikhailova
Southern Scientific Center
Email: mikhail@ipoc.rsu.ru
Russian Federation, ul. Chekhova 41, Rostov-on-Don, 344006
V. V. Tkachev
Institute of Problems of Chemical Physics
Email: mikhail@ipoc.rsu.ru
Russian Federation, Rostov-on-Don
S. M. Aldoshin
Institute of Problems of Chemical Physics
Email: mikhail@ipoc.rsu.ru
Russian Federation, Rostov-on-Don
V. I. Minkin
Scientific Research Institute of Physical and Organic Chemistry
Email: mikhail@ipoc.rsu.ru
Russian Federation, Rostov-on-Don