Synthesis, solvent interactions and computational study of monocarbohydrazones
Само за регистроване кориснике
2020
Аутори
Mrđan, Gorana S.Matijević, Borko M.
Vastag, Gyongyi
Božić, Aleksandra R.
Marinković, Aleksandar
Milčić, Miloš
Stojiljković, Ivana
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Carbohydrazones are compounds that are increasingly studied due to their wide potential biological activity. Monocarbohydrazones (mCHs), as one of the carbohydrazone derivatives, so far have been poorly investigated. For a more detailed study, in this paper, eighteen compounds of monocarbohydrazones (eight known and ten newly synthesized derivatives) were synthesized and characterized using NMR and IR spectroscopy. As carbohydrazones show E/Z isomerization caused by the presence of the imino group, some of the synthesized mCHs are in the form of a mixture of these two isomers. The effects of specific and nonspecific solvent-solute interactions on the UV absorption maxima shifts were evaluated using linear free energy relationships principles, i.e., using Kamlet-Taft's and Catalan's models. For more information about interactions between dissolved substance and the surrounding medium, correlations have been made with Hansen's solubility parameters. The influence of the structure on the ...spectral behavior of the compounds tested was interpreted using Hammett's equation. Experimentally obtained physicochemical properties of mCHs were compared to and confirmed with computational methods that included TD-DFT calculations and MP2 geometry optimizations. Graphic abstract
Кључне речи:
Monocarbohydrazones / Solvent interactions / Substituent effects / Molecular geometry optimization / TDF calculationsИзвор:
Chemical Papers, 2020, 74, 8, 2653-2674Издавач:
- Springer International Publishing Ag, Cham
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1007/s11696-020-01106-4
ISSN: 2585-7290
WoS: 000516389000002
Scopus: 2-s2.0-85080871420
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Mrđan, Gorana S. AU - Matijević, Borko M. AU - Vastag, Gyongyi AU - Božić, Aleksandra R. AU - Marinković, Aleksandar AU - Milčić, Miloš AU - Stojiljković, Ivana PY - 2020 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4497 AB - Carbohydrazones are compounds that are increasingly studied due to their wide potential biological activity. Monocarbohydrazones (mCHs), as one of the carbohydrazone derivatives, so far have been poorly investigated. For a more detailed study, in this paper, eighteen compounds of monocarbohydrazones (eight known and ten newly synthesized derivatives) were synthesized and characterized using NMR and IR spectroscopy. As carbohydrazones show E/Z isomerization caused by the presence of the imino group, some of the synthesized mCHs are in the form of a mixture of these two isomers. The effects of specific and nonspecific solvent-solute interactions on the UV absorption maxima shifts were evaluated using linear free energy relationships principles, i.e., using Kamlet-Taft's and Catalan's models. For more information about interactions between dissolved substance and the surrounding medium, correlations have been made with Hansen's solubility parameters. The influence of the structure on the spectral behavior of the compounds tested was interpreted using Hammett's equation. Experimentally obtained physicochemical properties of mCHs were compared to and confirmed with computational methods that included TD-DFT calculations and MP2 geometry optimizations. Graphic abstract PB - Springer International Publishing Ag, Cham T2 - Chemical Papers T1 - Synthesis, solvent interactions and computational study of monocarbohydrazones EP - 2674 IS - 8 SP - 2653 VL - 74 DO - 10.1007/s11696-020-01106-4 ER -
@article{ author = "Mrđan, Gorana S. and Matijević, Borko M. and Vastag, Gyongyi and Božić, Aleksandra R. and Marinković, Aleksandar and Milčić, Miloš and Stojiljković, Ivana", year = "2020", abstract = "Carbohydrazones are compounds that are increasingly studied due to their wide potential biological activity. Monocarbohydrazones (mCHs), as one of the carbohydrazone derivatives, so far have been poorly investigated. For a more detailed study, in this paper, eighteen compounds of monocarbohydrazones (eight known and ten newly synthesized derivatives) were synthesized and characterized using NMR and IR spectroscopy. As carbohydrazones show E/Z isomerization caused by the presence of the imino group, some of the synthesized mCHs are in the form of a mixture of these two isomers. The effects of specific and nonspecific solvent-solute interactions on the UV absorption maxima shifts were evaluated using linear free energy relationships principles, i.e., using Kamlet-Taft's and Catalan's models. For more information about interactions between dissolved substance and the surrounding medium, correlations have been made with Hansen's solubility parameters. The influence of the structure on the spectral behavior of the compounds tested was interpreted using Hammett's equation. Experimentally obtained physicochemical properties of mCHs were compared to and confirmed with computational methods that included TD-DFT calculations and MP2 geometry optimizations. Graphic abstract", publisher = "Springer International Publishing Ag, Cham", journal = "Chemical Papers", title = "Synthesis, solvent interactions and computational study of monocarbohydrazones", pages = "2674-2653", number = "8", volume = "74", doi = "10.1007/s11696-020-01106-4" }
Mrđan, G. S., Matijević, B. M., Vastag, G., Božić, A. R., Marinković, A., Milčić, M.,& Stojiljković, I.. (2020). Synthesis, solvent interactions and computational study of monocarbohydrazones. in Chemical Papers Springer International Publishing Ag, Cham., 74(8), 2653-2674. https://doi.org/10.1007/s11696-020-01106-4
Mrđan GS, Matijević BM, Vastag G, Božić AR, Marinković A, Milčić M, Stojiljković I. Synthesis, solvent interactions and computational study of monocarbohydrazones. in Chemical Papers. 2020;74(8):2653-2674. doi:10.1007/s11696-020-01106-4 .
Mrđan, Gorana S., Matijević, Borko M., Vastag, Gyongyi, Božić, Aleksandra R., Marinković, Aleksandar, Milčić, Miloš, Stojiljković, Ivana, "Synthesis, solvent interactions and computational study of monocarbohydrazones" in Chemical Papers, 74, no. 8 (2020):2653-2674, https://doi.org/10.1007/s11696-020-01106-4 . .