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Linear free energy relationships of the 1H and 13C NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones

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2009
Authors
Marinković, Aleksandar D.
Jovanović, Bratislav Ž.
Todorović, Nina
Juranić, Ivan
Article (Published version)
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Abstract
Linear free energy relationships (LFER) were applied to the 1H and 13C NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones. The correlation analysis for the substituent-induced chemical shifts (SCS) with inductive (σI), and various resonance (σR) parameters were carried out using SSP (single substituent parameter), DSP (dual substituent parameter), and DSP-NLR (dual substituent parameter non-linear resonance) methods, as well as by multiple regression analysis. The presented calculation accounts satisfactorily for the polar and resonance substituent effects operating at pyridone carbon atoms. Negative ρ values were found for several correlations (reverse substituent effect). The conformations of investigated compounds have been studied by the use of semi-empirical MO-PM6 method and B3LYP density functional (DFT) hybrid methods. The twist of the plane of 4-substituted phenyl ring (θ1) is determined by electronic substituent effects, while the angles θ2 are almo...st constant.

Keywords:
3-Cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones / Direct polarization / Extended polarization / Field effect / LFER
Source:
Journal of Molecular Structure, 2009, 920, 1-3, 90-96
Publisher:
  • Elsevier
Projects:
  • Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-142063)
  • Synthesis, characterization and activity of organic and coordination composition and their application in (bio) nanotechnology (RS-142010)

DOI: 10.1016/j.molstruc.2008.10.018

ISSN: 0022-2860

WoS: 000264251400014

Scopus: 2-s2.0-59849129561
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/603
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