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
TY - JOUR
AU - Mrdjan, Gorana S.
AU - Matijević, Borko M.
AU - Vastag, Gyongyi Gy
AU - Božić, Aleksandra R.
AU - Marinković, Aleksandar D.
AU - Milcić, Miloš K.
AU - Stojiljković, Ivana
PY - 2020
UR - https://omorika.sfb.bg.ac.rs/handle/123456789/1135
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
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
UR - conv_1481
ER -
@article{
author = "Mrdjan, Gorana S. and Matijević, Borko M. and Vastag, Gyongyi Gy and Božić, Aleksandra R. and Marinković, Aleksandar D. and Milcić, Miloš K. 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",
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",
url = "conv_1481"
}
Mrdjan, G. S., Matijević, B. M., Vastag, G. G., Božić, A. R., Marinković, A. D., Milcić, M. K.,& Stojiljković, I.. (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
conv_1481
Mrdjan GS, Matijević BM, Vastag GG, Božić AR, Marinković AD, Milcić MK, 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
conv_1481 .
Mrdjan, Gorana S., Matijević, Borko M., Vastag, Gyongyi Gy, Božić, Aleksandra R., Marinković, Aleksandar D., Milcić, Miloš K., 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 .,
conv_1481 .
