Linear free energy relationships of the H-1 and C-13 NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones
Abstract
Linear free energy relationships (LFER) were applied to the H-1 and C-13 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 (sigma(1)), and various resonance (sigma(R)) 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 rho 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 (theta(1)) is determined by electronic substituent effects, while t...he angles theta(2) are almost constant.
Keywords:
3-Cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones / LFER / Direct polarization / Extended polarization / Field effectSource:
Journal of Molecular Structure, 2009, 920, 1-3, 90-96Publisher:
- Elsevier Science Bv, Amsterdam
Funding / 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
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Marinković, Aleksandar AU - Jovanović, Bratislav Ž. AU - Todorović, Nina AU - Juranić, Ivan PY - 2009 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1480 AB - Linear free energy relationships (LFER) were applied to the H-1 and C-13 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 (sigma(1)), and various resonance (sigma(R)) 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 rho 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 (theta(1)) is determined by electronic substituent effects, while the angles theta(2) are almost constant. PB - Elsevier Science Bv, Amsterdam T2 - Journal of Molecular Structure T1 - Linear free energy relationships of the H-1 and C-13 NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones EP - 96 IS - 1-3 SP - 90 VL - 920 DO - 10.1016/j.molstruc.2008.10.018 ER -
@article{ author = "Marinković, Aleksandar and Jovanović, Bratislav Ž. and Todorović, Nina and Juranić, Ivan", year = "2009", abstract = "Linear free energy relationships (LFER) were applied to the H-1 and C-13 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 (sigma(1)), and various resonance (sigma(R)) 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 rho 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 (theta(1)) is determined by electronic substituent effects, while the angles theta(2) are almost constant.", publisher = "Elsevier Science Bv, Amsterdam", journal = "Journal of Molecular Structure", title = "Linear free energy relationships of the H-1 and C-13 NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones", pages = "96-90", number = "1-3", volume = "920", doi = "10.1016/j.molstruc.2008.10.018" }
Marinković, A., Jovanović, B. Ž., Todorović, N.,& Juranić, I.. (2009). Linear free energy relationships of the H-1 and C-13 NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones. in Journal of Molecular Structure Elsevier Science Bv, Amsterdam., 920(1-3), 90-96. https://doi.org/10.1016/j.molstruc.2008.10.018
Marinković A, Jovanović BŽ, Todorović N, Juranić I. Linear free energy relationships of the H-1 and C-13 NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones. in Journal of Molecular Structure. 2009;920(1-3):90-96. doi:10.1016/j.molstruc.2008.10.018 .
Marinković, Aleksandar, Jovanović, Bratislav Ž., Todorović, Nina, Juranić, Ivan, "Linear free energy relationships of the H-1 and C-13 NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones" in Journal of Molecular Structure, 920, no. 1-3 (2009):90-96, https://doi.org/10.1016/j.molstruc.2008.10.018 . .