N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study
2015
Authors
Matijević, Borko M.Vaštag, Đenđi Đ.
Apostolov, Suzana L.
Milčić, Miloš K.
Marinković, Aleksandar
Petrović, Slobodan D.
Article (Published version)
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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.
Keywords:
Bader' analysis / Molecular geometry optimization / N-(substituted phenyl)-2-chloroacetamides / Solvent effects / Substituent effects / UV absorption spectraSource:
Arabian Journal of Chemistry, 2015Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-MESTD-Basic Research (BR or ON)-172013)
Note:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3386
DOI: 10.1016/j.arabjc.2015.09.008
ISSN: 1878-5352
WoS: 000504900300159
Scopus: 2-s2.0-84951804933
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Matijević, Borko M. AU - Vaštag, Đenđi Đ. AU - Apostolov, Suzana L. AU - Milčić, Miloš K. AU - Marinković, Aleksandar AU - Petrović, Slobodan D. PY - 2015 UR - https://cherry.chem.bg.ac.rs/handle/123456789/293 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. T2 - Arabian Journal of Chemistry T1 - N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study DO - 10.1016/j.arabjc.2015.09.008 ER -
@article{ author = "Matijević, Borko M. and Vaštag, Đenđi Đ. and Apostolov, Suzana L. and Milčić, Miloš K. and Marinković, Aleksandar and Petrović, Slobodan D.", year = "2015", 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.", journal = "Arabian Journal of Chemistry", title = "N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study", doi = "10.1016/j.arabjc.2015.09.008" }
Matijević, B. M., Vaštag, Đ. Đ., Apostolov, S. L., Milčić, M. K., Marinković, A.,& Petrović, S. D.. (2015). N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study. in Arabian Journal of Chemistry. https://doi.org/10.1016/j.arabjc.2015.09.008
Matijević BM, Vaštag ĐĐ, Apostolov SL, Milčić MK, Marinković A, Petrović SD. N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study. in Arabian Journal of Chemistry. 2015;. doi:10.1016/j.arabjc.2015.09.008 .
Matijević, Borko M., Vaštag, Đenđi Đ., Apostolov, Suzana L., Milčić, Miloš K., Marinković, Aleksandar, Petrović, Slobodan D., "N-(substituted phenyl)-2-chloroacetamides: LSER and LFER study" in Arabian Journal of Chemistry (2015), https://doi.org/10.1016/j.arabjc.2015.09.008 . .