Linear free energy relationships of the 1H and 13C NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones
Само за регистроване кориснике
2009
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
3-Cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones / Direct polarization / Extended polarization / Field effect / LFERИзвор:
Journal of Molecular Structure, 2009, 920, 1-3, 90-96Издавач:
- Elsevier
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-MPN2006-2010-142063)
- Синтеза, карактеризација и активност органских и координационих једињења и њихова примена у (био)нанотехнологији (RS-MESTD-MPN2006-2010-142010)
DOI: 10.1016/j.molstruc.2008.10.018
ISSN: 0022-2860
WoS: 000264251400014
Scopus: 2-s2.0-59849129561
Институција/група
IHTMTY - JOUR AU - Marinković, Aleksandar D. AU - Jovanović, Bratislav Ž. AU - Todorović, Nina AU - Juranić, Ivan PY - 2009 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/603 AB - 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 almost constant. PB - Elsevier T2 - Journal of Molecular Structure T1 - Linear free energy relationships of the 1H and 13C NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones VL - 920 IS - 1-3 SP - 90 EP - 96 DO - 10.1016/j.molstruc.2008.10.018 ER -
@article{ author = "Marinković, Aleksandar D. and Jovanović, Bratislav Ž. and Todorović, Nina and Juranić, Ivan", year = "2009", 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 almost constant.", publisher = "Elsevier", journal = "Journal of Molecular Structure", title = "Linear free energy relationships of the 1H and 13C NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones", volume = "920", number = "1-3", pages = "90-96", doi = "10.1016/j.molstruc.2008.10.018" }
Marinković, A. D., Jovanović, B. Ž., Todorović, N.,& Juranić, I.. (2009). Linear free energy relationships of the 1H and 13C NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones. in Journal of Molecular Structure Elsevier., 920(1-3), 90-96. https://doi.org/10.1016/j.molstruc.2008.10.018
Marinković AD, Jovanović BŽ, Todorović N, Juranić I. Linear free energy relationships of the 1H and 13C 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 D., Jovanović, Bratislav Ž., Todorović, Nina, Juranić, Ivan, "Linear free energy relationships of the 1H and 13C 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 . .