This work contributes to theoretical chemistry’s knowledge of benzimidazole-hydrazide-hydrazone. Indeed, hydrazides-hydrazones-benzimidazoles have shown anticancer, antibacterial, antiparasitic activities, and many other activities. A benzimidazole-hydrazide-hydrazone compound can exhibit four conformers: E/Z synperiplanar (Esp, Zsp) and E/Z antiperiplanar (Eap, Zap). Studies have indicated that the prevalence of these compounds is attributed to their stability and their tendency to readily bind to DNA. A theoretical study with advanced methods would make it possible to evaluate the stability of benzimidazole-hydrazide-hydrazone conformers. Therefore, we carried out this theoretical study on the conformers of two benzimidazoles-hydrazides-hydrazones denoted C1 and C2 wich differ by the presence of fluorine atom in the structure of C2. Specifically, we analyze the stability and the reactivity of the compounds based on the dipole moment, Gibbs free energy, HOMO and LUMO energies and UV-visible. For this purpose, calculations were performed in gas phase and DMSO using DFT and TD-DFT methods at the B3LYP/6-311+G(d, p) level theory. The dipole moment values show that Zap conformer is the most polar for both compounds. The Gibbs free energy indicate that Esp conformer emerges as the most stable for both compounds in both phases. The energy gap (ELUMO-EHOMO) and TD-DFT results suggest that Esp conformer is the most reactive conformer for the two compounds.
| Published in | International Journal of Computational and Theoretical Chemistry (Volume 12, Issue 1) |
| DOI | 10.11648/j.ijctc.20241201.12 |
| Page(s) | 10-17 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2024. Published by Science Publishing Group |
Benzimidazole, Hydrazide-Hydrazone, Stability, B3LYP
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APA Style
Assoma, A. B., Bede, A. L., Achi, P., Coulibali, S. (2024). Stability and Reactivity of Two Benzimidazole Hydrazide-Hydrazone Compounds: A Theoretical Study by DFT Method. International Journal of Computational and Theoretical Chemistry, 12(1), 10-17. https://doi.org/10.11648/j.ijctc.20241201.12
ACS Style
Assoma, A. B.; Bede, A. L.; Achi, P.; Coulibali, S. Stability and Reactivity of Two Benzimidazole Hydrazide-Hydrazone Compounds: A Theoretical Study by DFT Method. Int. J. Comput. Theor. Chem. 2024, 12(1), 10-17. doi: 10.11648/j.ijctc.20241201.12
AMA Style
Assoma AB, Bede AL, Achi P, Coulibali S. Stability and Reactivity of Two Benzimidazole Hydrazide-Hydrazone Compounds: A Theoretical Study by DFT Method. Int J Comput Theor Chem. 2024;12(1):10-17. doi: 10.11648/j.ijctc.20241201.12
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Download@article{10.11648/j.ijctc.20241201.12,
author = {Amon Benjamine Assoma and Affoué Lucie Bede and Patrick-Armand Achi and Siomenan Coulibali},
title = {Stability and Reactivity of Two Benzimidazole Hydrazide-Hydrazone Compounds: A Theoretical Study by DFT Method
},
journal = {International Journal of Computational and Theoretical Chemistry},
volume = {12},
number = {1},
pages = {10-17},
doi = {10.11648/j.ijctc.20241201.12},
url = {https://doi.org/10.11648/j.ijctc.20241201.12},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijctc.20241201.12},
abstract = {This work contributes to theoretical chemistry’s knowledge of benzimidazole-hydrazide-hydrazone. Indeed, hydrazides-hydrazones-benzimidazoles have shown anticancer, antibacterial, antiparasitic activities, and many other activities. A benzimidazole-hydrazide-hydrazone compound can exhibit four conformers: E/Z synperiplanar (Esp, Zsp) and E/Z antiperiplanar (Eap, Zap). Studies have indicated that the prevalence of these compounds is attributed to their stability and their tendency to readily bind to DNA. A theoretical study with advanced methods would make it possible to evaluate the stability of benzimidazole-hydrazide-hydrazone conformers. Therefore, we carried out this theoretical study on the conformers of two benzimidazoles-hydrazides-hydrazones denoted C1 and C2 wich differ by the presence of fluorine atom in the structure of C2. Specifically, we analyze the stability and the reactivity of the compounds based on the dipole moment, Gibbs free energy, HOMO and LUMO energies and UV-visible. For this purpose, calculations were performed in gas phase and DMSO using DFT and TD-DFT methods at the B3LYP/6-311+G(d, p) level theory. The dipole moment values show that Zap conformer is the most polar for both compounds. The Gibbs free energy indicate that Esp conformer emerges as the most stable for both compounds in both phases. The energy gap (ELUMO-EHOMO) and TD-DFT results suggest that Esp conformer is the most reactive conformer for the two compounds.
},
year = {2024}
}
TY - JOUR T1 - Stability and Reactivity of Two Benzimidazole Hydrazide-Hydrazone Compounds: A Theoretical Study by DFT Method AU - Amon Benjamine Assoma AU - Affoué Lucie Bede AU - Patrick-Armand Achi AU - Siomenan Coulibali Y1 - 2024/05/24 PY - 2024 N1 - https://doi.org/10.11648/j.ijctc.20241201.12 DO - 10.11648/j.ijctc.20241201.12 T2 - International Journal of Computational and Theoretical Chemistry JF - International Journal of Computational and Theoretical Chemistry JO - International Journal of Computational and Theoretical Chemistry SP - 10 EP - 17 PB - Science Publishing Group SN - 2376-7308 UR - https://doi.org/10.11648/j.ijctc.20241201.12 AB - This work contributes to theoretical chemistry’s knowledge of benzimidazole-hydrazide-hydrazone. Indeed, hydrazides-hydrazones-benzimidazoles have shown anticancer, antibacterial, antiparasitic activities, and many other activities. A benzimidazole-hydrazide-hydrazone compound can exhibit four conformers: E/Z synperiplanar (Esp, Zsp) and E/Z antiperiplanar (Eap, Zap). Studies have indicated that the prevalence of these compounds is attributed to their stability and their tendency to readily bind to DNA. A theoretical study with advanced methods would make it possible to evaluate the stability of benzimidazole-hydrazide-hydrazone conformers. Therefore, we carried out this theoretical study on the conformers of two benzimidazoles-hydrazides-hydrazones denoted C1 and C2 wich differ by the presence of fluorine atom in the structure of C2. Specifically, we analyze the stability and the reactivity of the compounds based on the dipole moment, Gibbs free energy, HOMO and LUMO energies and UV-visible. For this purpose, calculations were performed in gas phase and DMSO using DFT and TD-DFT methods at the B3LYP/6-311+G(d, p) level theory. The dipole moment values show that Zap conformer is the most polar for both compounds. The Gibbs free energy indicate that Esp conformer emerges as the most stable for both compounds in both phases. The energy gap (ELUMO-EHOMO) and TD-DFT results suggest that Esp conformer is the most reactive conformer for the two compounds. VL - 12 IS - 1 ER -
Unit of Formation and Research of Sciences of Structures of Matter and Technology (UFR-SSMT), University Felix Houphouet-Boigny, Abidjan, Ivory Coast
Unit of Formation and Research of Sciences of Structures of Matter and Technology (UFR-SSMT), University Felix Houphouet-Boigny, Abidjan, Ivory Coast
Preparatory School for Higher Education, Institute National Polytechnic Felix Houphouet-Boigny (INP-HB), Yamoussoukro, Ivory Coast
Unit of Formation and Research of Sciences of Structures of Matter and Technology (UFR-SSMT), University Felix Houphouet-Boigny, Abidjan, Ivory Coast
