Synthesis, solvent interactions and computational study of monocarbohydrazones
Samo za registrovane korisnike
2020
Autori
Mrđan, Gorana S.Matijević, Borko M.
Vastag, Gyöngyi Gy.
Božić, Aleksandra R.
Marinković, Aleksandar
Milčić, Miloš K.
Stojiljković, Ivana N.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Izvor:
Chemical Papers, 2020, 74, 8, 2653-2674Finansiranje / projekti:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1007/s11696-020-01106-4
ISSN: 0366-6352
WoS: 000516389000002
Scopus: 2-s2.0-85080871420
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Mrđan, Gorana S. AU - Matijević, Borko M. AU - Vastag, Gyöngyi Gy. AU - Božić, Aleksandra R. AU - Marinković, Aleksandar AU - Milčić, Miloš K. AU - Stojiljković, Ivana N. PY - 2020 UR - https://doi.org/10.1007/s11696-020-01106-4 UR - https://cherry.chem.bg.ac.rs/handle/123456789/4280 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. T2 - Chemical Papers T1 - Synthesis, solvent interactions and computational study of monocarbohydrazones VL - 74 IS - 8 SP - 2653 EP - 2674 DO - 10.1007/s11696-020-01106-4 ER -
@article{ author = "Mrđan, Gorana S. and Matijević, Borko M. and Vastag, Gyöngyi Gy. and Božić, Aleksandra R. and Marinković, Aleksandar and Milčić, Miloš K. and Stojiljković, Ivana N.", 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.", journal = "Chemical Papers", title = "Synthesis, solvent interactions and computational study of monocarbohydrazones", volume = "74", number = "8", pages = "2653-2674", doi = "10.1007/s11696-020-01106-4" }
Mrđan, G. S., Matijević, B. M., Vastag, G. Gy., Božić, A. R., Marinković, A., Milčić, M. K.,& Stojiljković, I. N.. (2020). Synthesis, solvent interactions and computational study of monocarbohydrazones. in Chemical Papers, 74(8), 2653-2674. https://doi.org/10.1007/s11696-020-01106-4
Mrđan GS, Matijević BM, Vastag GG, Božić AR, Marinković A, Milčić MK, Stojiljković IN. 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, Gyöngyi Gy., Božić, Aleksandra R., Marinković, Aleksandar, Milčić, Miloš K., Stojiljković, Ivana N., "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 . .