Quantum-chemical simulation of structure and conformational flexibility of 5,7-di(tert-butyl)-2-(8-hydroxyquinolin-2-yl)-1,3-tropolone View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2016-06

AUTHORS

G. A. Dushenko, I. E. Mikhailov, Yu. M. Artyushkina, O. I. Mikhailova, V. V. Tkachev, S. M. Aldoshin, V. I. Minkin

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). More... »

PAGES

1306-1313

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070363216060141

DOI

http://dx.doi.org/10.1134/s1070363216060141

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1010805403


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