Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives
Аутори
Mrđan, Gorana S.Vastag, Gyöngyi Gy.
Škorić, Dušan Đ.
Radanović, Mirjana M.
Verbić, Tatjana
Milčić, Miloš K.
Stojiljković, Ivana N.
Marković, Olivera S.
Matijević, Borko M.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Derivatives of thiocarbohydrazone studied so far have shown great biological activity such as antioxidant, antimicrobial, and anticancer. Most of these compounds are bis-substituted derivatives, while monothiocarbohydrazones are much less investigated. Еighteen monothiocarbohydrazones were synthesized and subjected to physicochemical characterization in order to facilitate the examination of their potential biological activity and application in future studies. The structure of synthesized derivatives was confirmed with NMR and FT–IR spectroscopy, and with elemental analysis. For one of the compounds, single-crystal X-ray diffraction analysis was performed. Specific and non-specific molecular interactions were interpreted by LSER principles, using Catalan’s model. For additional information about the dominance and influence of the interactions presented, correlations with Hansen’s solubility parameters were calculated. Influence of the type and position of the substituent on absorption... maxima was determined with LFER (linear free-energy relationship) principles, using Hammett’s equation. Acidity constants of the synthesized compounds were theoretically calculated and experimentally determined. Moreover, the excitation of a molecule by a photon of UV–Vis light was interpreted by time-dependent density functional theory (TD–DFT) calculations of UV absorption bands, and intramolecular charge transfer (ICT) was quantified by calculations of the charge transfer distances (DCT). © 2021, The Author(s), under exclusive licence to Springer Science+Business Media, LLC part of Springer Nature.
Кључне речи:
Acidity constants / LFER / LSER / Monothiocarbohydrazones / TD–DFT / X-rayИзвор:
Structural Chemistry, 2021, 32, 3, 1231-1245Издавач:
- Springer Nature
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200125 (Универзитет у Новом Саду, Природно-математички факултет) (RS-MESTD-inst-2020-200125)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200168 (Универзитет у Београду, Хемијски факултет) (RS-MESTD-inst-2020-200168)
Напомена:
- Supplementary material: https://cherry.chem.bg.ac.rs/handle/123456789/4454
Повезане информације:
DOI: 10.1007/s11224-020-01700-y
ISSN: 1040-0400
WoS: 000605937400007
Scopus: 2-s2.0-85099105614
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Mrđan, Gorana S. AU - Vastag, Gyöngyi Gy. AU - Škorić, Dušan Đ. AU - Radanović, Mirjana M. AU - Verbić, Tatjana AU - Milčić, Miloš K. AU - Stojiljković, Ivana N. AU - Marković, Olivera S. AU - Matijević, Borko M. PY - 2021 UR - https://cherry.chem.bg.ac.rs/handle/123456789/4453 AB - Derivatives of thiocarbohydrazone studied so far have shown great biological activity such as antioxidant, antimicrobial, and anticancer. Most of these compounds are bis-substituted derivatives, while monothiocarbohydrazones are much less investigated. Еighteen monothiocarbohydrazones were synthesized and subjected to physicochemical characterization in order to facilitate the examination of their potential biological activity and application in future studies. The structure of synthesized derivatives was confirmed with NMR and FT–IR spectroscopy, and with elemental analysis. For one of the compounds, single-crystal X-ray diffraction analysis was performed. Specific and non-specific molecular interactions were interpreted by LSER principles, using Catalan’s model. For additional information about the dominance and influence of the interactions presented, correlations with Hansen’s solubility parameters were calculated. Influence of the type and position of the substituent on absorption maxima was determined with LFER (linear free-energy relationship) principles, using Hammett’s equation. Acidity constants of the synthesized compounds were theoretically calculated and experimentally determined. Moreover, the excitation of a molecule by a photon of UV–Vis light was interpreted by time-dependent density functional theory (TD–DFT) calculations of UV absorption bands, and intramolecular charge transfer (ICT) was quantified by calculations of the charge transfer distances (DCT). © 2021, The Author(s), under exclusive licence to Springer Science+Business Media, LLC part of Springer Nature. PB - Springer Nature T2 - Structural Chemistry T2 - Structural Chemistry T2 - Structural Chemistry T1 - Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives VL - 32 IS - 3 SP - 1231 EP - 1245 DO - 10.1007/s11224-020-01700-y ER -
@article{ author = "Mrđan, Gorana S. and Vastag, Gyöngyi Gy. and Škorić, Dušan Đ. and Radanović, Mirjana M. and Verbić, Tatjana and Milčić, Miloš K. and Stojiljković, Ivana N. and Marković, Olivera S. and Matijević, Borko M.", year = "2021", abstract = "Derivatives of thiocarbohydrazone studied so far have shown great biological activity such as antioxidant, antimicrobial, and anticancer. Most of these compounds are bis-substituted derivatives, while monothiocarbohydrazones are much less investigated. Еighteen monothiocarbohydrazones were synthesized and subjected to physicochemical characterization in order to facilitate the examination of their potential biological activity and application in future studies. The structure of synthesized derivatives was confirmed with NMR and FT–IR spectroscopy, and with elemental analysis. For one of the compounds, single-crystal X-ray diffraction analysis was performed. Specific and non-specific molecular interactions were interpreted by LSER principles, using Catalan’s model. For additional information about the dominance and influence of the interactions presented, correlations with Hansen’s solubility parameters were calculated. Influence of the type and position of the substituent on absorption maxima was determined with LFER (linear free-energy relationship) principles, using Hammett’s equation. Acidity constants of the synthesized compounds were theoretically calculated and experimentally determined. Moreover, the excitation of a molecule by a photon of UV–Vis light was interpreted by time-dependent density functional theory (TD–DFT) calculations of UV absorption bands, and intramolecular charge transfer (ICT) was quantified by calculations of the charge transfer distances (DCT). © 2021, The Author(s), under exclusive licence to Springer Science+Business Media, LLC part of Springer Nature.", publisher = "Springer Nature", journal = "Structural Chemistry, Structural Chemistry, Structural Chemistry", title = "Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives", volume = "32", number = "3", pages = "1231-1245", doi = "10.1007/s11224-020-01700-y" }
Mrđan, G. S., Vastag, G. Gy., Škorić, D. Đ., Radanović, M. M., Verbić, T., Milčić, M. K., Stojiljković, I. N., Marković, O. S.,& Matijević, B. M.. (2021). Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives. in Structural Chemistry Springer Nature., 32(3), 1231-1245. https://doi.org/10.1007/s11224-020-01700-y
Mrđan GS, Vastag GG, Škorić DĐ, Radanović MM, Verbić T, Milčić MK, Stojiljković IN, Marković OS, Matijević BM. Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives. in Structural Chemistry. 2021;32(3):1231-1245. doi:10.1007/s11224-020-01700-y .
Mrđan, Gorana S., Vastag, Gyöngyi Gy., Škorić, Dušan Đ., Radanović, Mirjana M., Verbić, Tatjana, Milčić, Miloš K., Stojiljković, Ivana N., Marković, Olivera S., Matijević, Borko M., "Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives" in Structural Chemistry, 32, no. 3 (2021):1231-1245, https://doi.org/10.1007/s11224-020-01700-y . .