The experimental and theoretical study of tautomerism of 3-substituted 2-methyl-quinoline-4 (1h)-ones

Authors

  • V. O. Zubkov National University of Pharmacy, Ukraine
  • O. B. Rozhenko Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • N. I. Ruschak SHHE «Ivano-Frankivsk National Medical University», Ukraine
  • S. I. Gritsenko National University of Pharmacy, Ukraine

DOI:

https://doi.org/10.24959/ophcj.16.892

Keywords:

quinoline-4(1H)-ones, tautomerism, 13C NMR-spectroscopy, quantum-chemical calculations

Abstract

4-Hydroxy-/4-oxo tautomerism in the series of 3-substituted 2-methyl-quinolin-4(1H)-ones has been studied by 13C NMR-spectroscopy and quantum-chemical methods in various approximations (restricted Hartree-Fock method, DFT and MP2) for the isolated molecules and for solutions using empirical correction of effects for solvents (PCM COSMO procedure). Substituents that are different in their nature have no significant influence on the value of the chemical shift of carbon in position C4 of the quinolone cycle. The only exception is the carbon shielding associated with the bromine atom in the molecule of 3-bromo-2-methyl-1,4-dihydroquinoline-4-one. Significant deshielding detected in all cases in 13C NMR-spectra of the carbon nuclei in position 4 of the ring is in favour of the existence of all derivatives studied as 4-oxo forms in DMSO-d6 solution. The experimental and calculated values for the chemical shift of carbon in position C4 of 4-oxo and 4-hydroxy isomers differ considerably and can be used as a criterion for assigning quinolin-4 (1H)-ones to a particular tautomeric form.

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Published

2016-06-21

How to Cite

(1)
Zubkov, V. O.; Rozhenko, O. B.; Ruschak, N. I.; Gritsenko, S. I. The Experimental and Theoretical Study of Tautomerism of 3-Substituted 2-Methyl-Quinoline-4 (1h)-Ones. J. Org. Pharm. Chem. 2016, 14, 53-59.

Issue

Vol. 14 No. 2(54) (2016)

Section

Original Researches

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