Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study
Аутори
Ajaj, IsmailAssaleh, Fathi H.
Markovski, Jasmina
Rančić, Milica
Brković, Danijela V
Milčić, Miloš
Marinković, Aleksandar
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
The state of the tautomeric equilibria of eleven arylazo pyridone dyes was evaluated from UV-Vis absorption spectra with the aid of the quantum mechanical modeling. NMR analysis and theoretical calculations, by using PCM/omega B97X-D/6-311G(d,p) method, confirmed that prepared compounds exist mainly in Hydrazo form. Internal hydrogen bonding in Hydrazo tautomer, analyzed by AIM topological analysis and total electron density at the bond critical point (BCP), confirmed a presence of strong hydrogen bond which contributes to higher stability of Hydrazo form. Linear solvation energy relationships (LSERs) rationalized solvent influence on solvatochromism of all compounds in Hydrazo form and K-T by using Kamlet-Taft model. Linear free energy relationships (LFERs) were applied to the substituent-inducedNMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Density plots over the highest occupied (HOMO) and lowest unoccupied molecular or...bitals (LUMO) energy surface provide information on the charge transfer during excitation. The molecular electrostatic potential (MEP) surface map was plotted over the optimized geometry of the molecules in order to visualize electron density distribution and explain origin of solvent/solute interactions.
Кључне речи:
Arylazo pyridone dye / UV-Vis spectra / Solvatochromism / Azo-Hydrazo tautomerismИзвор:
Arabian Journal of Chemistry, 2019, 12, 8, 3463-3478Издавач:
- Elsevier, Amsterdam
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1016/j.arabjc.2015.08.029
ISSN: 1878-5352
WoS: 000504900300166
Scopus: 2-s2.0-85028929085
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Ajaj, Ismail AU - Assaleh, Fathi H. AU - Markovski, Jasmina AU - Rančić, Milica AU - Brković, Danijela V AU - Milčić, Miloš AU - Marinković, Aleksandar PY - 2019 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4130 AB - The state of the tautomeric equilibria of eleven arylazo pyridone dyes was evaluated from UV-Vis absorption spectra with the aid of the quantum mechanical modeling. NMR analysis and theoretical calculations, by using PCM/omega B97X-D/6-311G(d,p) method, confirmed that prepared compounds exist mainly in Hydrazo form. Internal hydrogen bonding in Hydrazo tautomer, analyzed by AIM topological analysis and total electron density at the bond critical point (BCP), confirmed a presence of strong hydrogen bond which contributes to higher stability of Hydrazo form. Linear solvation energy relationships (LSERs) rationalized solvent influence on solvatochromism of all compounds in Hydrazo form and K-T by using Kamlet-Taft model. Linear free energy relationships (LFERs) were applied to the substituent-inducedNMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Density plots over the highest occupied (HOMO) and lowest unoccupied molecular orbitals (LUMO) energy surface provide information on the charge transfer during excitation. The molecular electrostatic potential (MEP) surface map was plotted over the optimized geometry of the molecules in order to visualize electron density distribution and explain origin of solvent/solute interactions. PB - Elsevier, Amsterdam T2 - Arabian Journal of Chemistry T1 - Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study EP - 3478 IS - 8 SP - 3463 VL - 12 DO - 10.1016/j.arabjc.2015.08.029 ER -
@article{ author = "Ajaj, Ismail and Assaleh, Fathi H. and Markovski, Jasmina and Rančić, Milica and Brković, Danijela V and Milčić, Miloš and Marinković, Aleksandar", year = "2019", abstract = "The state of the tautomeric equilibria of eleven arylazo pyridone dyes was evaluated from UV-Vis absorption spectra with the aid of the quantum mechanical modeling. NMR analysis and theoretical calculations, by using PCM/omega B97X-D/6-311G(d,p) method, confirmed that prepared compounds exist mainly in Hydrazo form. Internal hydrogen bonding in Hydrazo tautomer, analyzed by AIM topological analysis and total electron density at the bond critical point (BCP), confirmed a presence of strong hydrogen bond which contributes to higher stability of Hydrazo form. Linear solvation energy relationships (LSERs) rationalized solvent influence on solvatochromism of all compounds in Hydrazo form and K-T by using Kamlet-Taft model. Linear free energy relationships (LFERs) were applied to the substituent-inducedNMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Density plots over the highest occupied (HOMO) and lowest unoccupied molecular orbitals (LUMO) energy surface provide information on the charge transfer during excitation. The molecular electrostatic potential (MEP) surface map was plotted over the optimized geometry of the molecules in order to visualize electron density distribution and explain origin of solvent/solute interactions.", publisher = "Elsevier, Amsterdam", journal = "Arabian Journal of Chemistry", title = "Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study", pages = "3478-3463", number = "8", volume = "12", doi = "10.1016/j.arabjc.2015.08.029" }
Ajaj, I., Assaleh, F. H., Markovski, J., Rančić, M., Brković, D. V., Milčić, M.,& Marinković, A.. (2019). Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study. in Arabian Journal of Chemistry Elsevier, Amsterdam., 12(8), 3463-3478. https://doi.org/10.1016/j.arabjc.2015.08.029
Ajaj I, Assaleh FH, Markovski J, Rančić M, Brković DV, Milčić M, Marinković A. Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study. in Arabian Journal of Chemistry. 2019;12(8):3463-3478. doi:10.1016/j.arabjc.2015.08.029 .
Ajaj, Ismail, Assaleh, Fathi H., Markovski, Jasmina, Rančić, Milica, Brković, Danijela V, Milčić, Miloš, Marinković, Aleksandar, "Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study" in Arabian Journal of Chemistry, 12, no. 8 (2019):3463-3478, https://doi.org/10.1016/j.arabjc.2015.08.029 . .