A Comprehensive Study of N-Butyl-1H-Benzimidazole
Imidazole derivatives have found wide application in organic and medicinal chemistry. In particular, benzimidazoles have proven biological activity as antiviral, antimicrobial, and antitumor agents. In this work, we experimentally and theoretically investigated N-Butyl-1H-benzimidazole. It has been...
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MDPI AG
2022-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/22/7864 |
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| author | Aleksandr S. Kazachenko Emine Tanış Feride Akman Mouna Medimagh Noureddine Issaoui Omar Al-Dossary Leda G. Bousiakou Anna S. Kazachenko Dmitry Zimonin Andrey M. Skripnikov |
| author_facet | Aleksandr S. Kazachenko Emine Tanış Feride Akman Mouna Medimagh Noureddine Issaoui Omar Al-Dossary Leda G. Bousiakou Anna S. Kazachenko Dmitry Zimonin Andrey M. Skripnikov |
| author_sort | Aleksandr S. Kazachenko |
| collection | DOAJ |
| description | Imidazole derivatives have found wide application in organic and medicinal chemistry. In particular, benzimidazoles have proven biological activity as antiviral, antimicrobial, and antitumor agents. In this work, we experimentally and theoretically investigated N-Butyl-1H-benzimidazole. It has been shown that the presence of a butyl substituent in the N position does not significantly affect the conjugation and structural organization of benzimidazole. The optimized molecular parameters were performed by the DFT/B3LYP method with 6-311++G(d,p) basis set. This level of theory shows excellent concurrence with the experimental data. The non-covalent interactions that existed within our compound N-Butyl-1H-benzimidazole were also analyzed by the AIM, RDG, ELF, and LOL topological methods. The color shades of the ELF and LOL maps confirm the presence of bonding and non-bonding electrons in N-Butyl-1H-benzimidazole. From DFT calculations, various methods such as molecular electrostatic potential (MEP), Fukui functions, Mulliken atomic charges, and frontier molecular orbital (HOMO-LUMO) were characterized. Furthermore, UV-Vis absorption and natural bond orbital (NBO) analysis were calculated. It is shown that the experimental and theoretical spectra of N-Butyl-1H-benzimidazole have a peak at 248 nm; in addition, the experimental spectrum has a peak near 295 nm. The NBO method shows that the delocalization of the aσ-electron from σ (C1–C2) is distributed into antibonding σ* (C1–C6), σ* (C1–N26), and σ* (C6–H11), which leads to stabilization energies of 4.63, 0.86, and 2.42 KJ/mol, respectively. Spectroscopic investigations of N-Butyl-1H-benzimidazole were carried out experimentally and theoretically to find FTIR vibrational spectra. |
| first_indexed | 2024-03-09T18:07:31Z |
| format | Article |
| id | doaj.art-fbb09cc6dd0c4ffc844021999f360722 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:07:31Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-fbb09cc6dd0c4ffc844021999f3607222023-11-24T09:22:26ZengMDPI AGMolecules1420-30492022-11-012722786410.3390/molecules27227864A Comprehensive Study of N-Butyl-1H-BenzimidazoleAleksandr S. Kazachenko0Emine Tanış1Feride Akman2Mouna Medimagh3Noureddine Issaoui4Omar Al-Dossary5Leda G. Bousiakou6Anna S. Kazachenko7Dmitry Zimonin8Andrey M. Skripnikov9School of Non-Ferrous Metals and Material Science, Siberian Federal University, Pr. Svobodny 79, 660041 Krasnoyarsk, RussiaDepartment of Electrical Electronics Engineering, Faculty of Engineering and Architecture, Kırşehir Ahi Evran University, Kırşehir 40100, TurkeyVocational School of Food, Agriculture and Livestock, University of Bingöl, Bingöl 12000, TurkeyLaboratory of Quantum and Statistical Physics (LR18ES18), Faculty of Sciences, University of Monastir, Monastir 5000, TunisiaLaboratory of Quantum and Statistical Physics (LR18ES18), Faculty of Sciences, University of Monastir, Monastir 5000, TunisiaDepartment of Physics and Astronomy, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaIMD Laboratories Co., R&D Section, Lefkippos Technology Park, NCSR Demokritos, P.O. Box 60037, 15130 Athens, GreeceSchool of Non-Ferrous Metals and Material Science, Siberian Federal University, Pr. Svobodny 79, 660041 Krasnoyarsk, RussiaSchool of Non-Ferrous Metals and Material Science, Siberian Federal University, Pr. Svobodny 79, 660041 Krasnoyarsk, RussiaSchool of Non-Ferrous Metals and Material Science, Siberian Federal University, Pr. Svobodny 79, 660041 Krasnoyarsk, RussiaImidazole derivatives have found wide application in organic and medicinal chemistry. In particular, benzimidazoles have proven biological activity as antiviral, antimicrobial, and antitumor agents. In this work, we experimentally and theoretically investigated N-Butyl-1H-benzimidazole. It has been shown that the presence of a butyl substituent in the N position does not significantly affect the conjugation and structural organization of benzimidazole. The optimized molecular parameters were performed by the DFT/B3LYP method with 6-311++G(d,p) basis set. This level of theory shows excellent concurrence with the experimental data. The non-covalent interactions that existed within our compound N-Butyl-1H-benzimidazole were also analyzed by the AIM, RDG, ELF, and LOL topological methods. The color shades of the ELF and LOL maps confirm the presence of bonding and non-bonding electrons in N-Butyl-1H-benzimidazole. From DFT calculations, various methods such as molecular electrostatic potential (MEP), Fukui functions, Mulliken atomic charges, and frontier molecular orbital (HOMO-LUMO) were characterized. Furthermore, UV-Vis absorption and natural bond orbital (NBO) analysis were calculated. It is shown that the experimental and theoretical spectra of N-Butyl-1H-benzimidazole have a peak at 248 nm; in addition, the experimental spectrum has a peak near 295 nm. The NBO method shows that the delocalization of the aσ-electron from σ (C1–C2) is distributed into antibonding σ* (C1–C6), σ* (C1–N26), and σ* (C6–H11), which leads to stabilization energies of 4.63, 0.86, and 2.42 KJ/mol, respectively. Spectroscopic investigations of N-Butyl-1H-benzimidazole were carried out experimentally and theoretically to find FTIR vibrational spectra.https://www.mdpi.com/1420-3049/27/22/7864N-butyl-1H-benzimidazolebenzimidazoleDFTAIMRDGELF |
| spellingShingle | Aleksandr S. Kazachenko Emine Tanış Feride Akman Mouna Medimagh Noureddine Issaoui Omar Al-Dossary Leda G. Bousiakou Anna S. Kazachenko Dmitry Zimonin Andrey M. Skripnikov A Comprehensive Study of N-Butyl-1H-Benzimidazole Molecules N-butyl-1H-benzimidazole benzimidazole DFT AIM RDG ELF |
| title | A Comprehensive Study of N-Butyl-1H-Benzimidazole |
| title_full | A Comprehensive Study of N-Butyl-1H-Benzimidazole |
| title_fullStr | A Comprehensive Study of N-Butyl-1H-Benzimidazole |
| title_full_unstemmed | A Comprehensive Study of N-Butyl-1H-Benzimidazole |
| title_short | A Comprehensive Study of N-Butyl-1H-Benzimidazole |
| title_sort | comprehensive study of n butyl 1h benzimidazole |
| topic | N-butyl-1H-benzimidazole benzimidazole DFT AIM RDG ELF |
| url | https://www.mdpi.com/1420-3049/27/22/7864 |
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