N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study
2019
Authors
Matijević, Borko M.Vaštag, Đenđi
Apostolov, Suzana
Milčić, Miloš
Marinković, Aleksandar
Petrović, Slobodan
Article (Published version)
Metadata
Show full item recordAbstract
The UV absorption spectra of twelve N-(substituted phenyl)-2-chloroacetamides were recorded in eighteen solvents. The effect of specific and non-specific solvent-solute interactions on the absorption maxima shifts was evaluated by using the Kamlet-Taft solvent parameter set, i.e. applying linear solvation energy relationships (LSER) principles. Optimized geometries and experimental results were interpreted by using DFT (B3LYP/6-311+G(d,p) method) and time-dependent density functional (TD-DFT) method. Overall electron density in both ground and excited state was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. It was found that both solvent and substituents cause appropriate change of the extent of conjugation in the molecules that further affect their intra-molecular charge transfer (ICT) character. Linear free energy relationships (LFERs) were applied to the substituent-induced NMR chemical shifts (SCS) using single substituent parameter (SSP) and du...al substituent parameter (DSP) model. Transmission mode of the electronic effects of substituent was discussed according to the results of theoretical calculations and results of LFER correlations. Comparative analysis of presented results with the ones published for structurally similar series of amide which contained cyano group, instead chlorine, provides additional information on the impact of present group to the properties of investigated compound.
Keywords:
N-(substituted phenyl)-2-chloroacetamides / UV absorption spectra / Solvent effects / Substituent effects / Molecular geometry optimization / Bader' analysisSource:
Arabian Journal of Chemistry, 2019, 12, 8, 3367-3379Publisher:
- Elsevier, Amsterdam
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1016/j.arabjc.2015.09.008
ISSN: 1878-5352
WoS: 000504900300159
Scopus: 2-s2.0-84951804933
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Matijević, Borko M. AU - Vaštag, Đenđi AU - Apostolov, Suzana AU - Milčić, Miloš AU - Marinković, Aleksandar AU - Petrović, Slobodan PY - 2019 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4116 AB - The UV absorption spectra of twelve N-(substituted phenyl)-2-chloroacetamides were recorded in eighteen solvents. The effect of specific and non-specific solvent-solute interactions on the absorption maxima shifts was evaluated by using the Kamlet-Taft solvent parameter set, i.e. applying linear solvation energy relationships (LSER) principles. Optimized geometries and experimental results were interpreted by using DFT (B3LYP/6-311+G(d,p) method) and time-dependent density functional (TD-DFT) method. Overall electron density in both ground and excited state was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. It was found that both solvent and substituents cause appropriate change of the extent of conjugation in the molecules that further affect their intra-molecular charge transfer (ICT) character. Linear free energy relationships (LFERs) were applied to the substituent-induced NMR chemical shifts (SCS) using single substituent parameter (SSP) and dual substituent parameter (DSP) model. Transmission mode of the electronic effects of substituent was discussed according to the results of theoretical calculations and results of LFER correlations. Comparative analysis of presented results with the ones published for structurally similar series of amide which contained cyano group, instead chlorine, provides additional information on the impact of present group to the properties of investigated compound. PB - Elsevier, Amsterdam T2 - Arabian Journal of Chemistry T1 - N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study EP - 3379 IS - 8 SP - 3367 VL - 12 DO - 10.1016/j.arabjc.2015.09.008 ER -
@article{ author = "Matijević, Borko M. and Vaštag, Đenđi and Apostolov, Suzana and Milčić, Miloš and Marinković, Aleksandar and Petrović, Slobodan", year = "2019", abstract = "The UV absorption spectra of twelve N-(substituted phenyl)-2-chloroacetamides were recorded in eighteen solvents. The effect of specific and non-specific solvent-solute interactions on the absorption maxima shifts was evaluated by using the Kamlet-Taft solvent parameter set, i.e. applying linear solvation energy relationships (LSER) principles. Optimized geometries and experimental results were interpreted by using DFT (B3LYP/6-311+G(d,p) method) and time-dependent density functional (TD-DFT) method. Overall electron density in both ground and excited state was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. It was found that both solvent and substituents cause appropriate change of the extent of conjugation in the molecules that further affect their intra-molecular charge transfer (ICT) character. Linear free energy relationships (LFERs) were applied to the substituent-induced NMR chemical shifts (SCS) using single substituent parameter (SSP) and dual substituent parameter (DSP) model. Transmission mode of the electronic effects of substituent was discussed according to the results of theoretical calculations and results of LFER correlations. Comparative analysis of presented results with the ones published for structurally similar series of amide which contained cyano group, instead chlorine, provides additional information on the impact of present group to the properties of investigated compound.", publisher = "Elsevier, Amsterdam", journal = "Arabian Journal of Chemistry", title = "N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study", pages = "3379-3367", number = "8", volume = "12", doi = "10.1016/j.arabjc.2015.09.008" }
Matijević, B. M., Vaštag, Đ., Apostolov, S., Milčić, M., Marinković, A.,& Petrović, S.. (2019). N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study. in Arabian Journal of Chemistry Elsevier, Amsterdam., 12(8), 3367-3379. https://doi.org/10.1016/j.arabjc.2015.09.008
Matijević BM, Vaštag Đ, Apostolov S, Milčić M, Marinković A, Petrović S. N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study. in Arabian Journal of Chemistry. 2019;12(8):3367-3379. doi:10.1016/j.arabjc.2015.09.008 .
Matijević, Borko M., Vaštag, Đenđi, Apostolov, Suzana, Milčić, Miloš, Marinković, Aleksandar, Petrović, Slobodan, "N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study" in Arabian Journal of Chemistry, 12, no. 8 (2019):3367-3379, https://doi.org/10.1016/j.arabjc.2015.09.008 . .