The 2-phenylbenzothiazole derivatives have antitumor activities. Work has shown that these derivatives have mesomeric forms. The electrophilic centers of these mesomers form adducts with the nucleophilic centers of deoxyribonucleic acid (DNA). These adducts destroy the tumor cells and prevent the proliferation of these. In this sense, the knowledge of electrophilic sites, nucleophiles and the capacity to protonate these derivatives is therefore useful if we want to know their future in the biological environment. Using DFT/B3LYP method associated with the bases 6-31G (d, p) and 6-31+G (d, p), this work aims at determining the preferential protonation site, the electrophilic and nucleophilic centers of six 2-phenylbenzothiazole. This study also analyzes the stability of these derivatives. Calculations are carried out in gas and aqueous phases. Results show that fluorinated derivatives are the most stable. 2-(4-aminophenyl) benzothiazoles are the most reactive. The atoms carbon C4, C5 and C6 of benzothiazole ring are the most electrophilic. Interactions of these derivatives with nucleophilic centers of deoxyribonucleic acid (DNA) will probably be at these atoms. Nitrogen sp2 (N1) of benzothiazole ring remains the most nucleophilic center and the preferential site of protonation in all the molecules studied. These results highlight the influence of the substituents on the basicity of the nitrogen sp2 (N1) and reactivity of the 2-phenylbenzothiazole derivatives studied.
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Modern Chemistry (Volume 7, Issue 3)
This article belongs to the Special Issue Advanced Journal of Chemistry |
| DOI | 10.11648/j.mc.20190703.14 |
| Page(s) | 65-72 |
| 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. |
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Copyright © The Author(s), 2019. Published by Science Publishing Group |
2-Phenylbenzothiazole, Energetic Gaps, Fukui Indices, Protonic Affinity, DFT/B3LYP
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APA Style
Bede Affoue Lucie, Kone Soleymane, N’Guessan Boka Robert, Yapo Kicho Denis, Ziao Nahosse. (2019). A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives. Modern Chemistry, 7(3), 65-72. https://doi.org/10.11648/j.mc.20190703.14
ACS Style
Bede Affoue Lucie; Kone Soleymane; N’Guessan Boka Robert; Yapo Kicho Denis; Ziao Nahosse. A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives. Mod. Chem. 2019, 7(3), 65-72. doi: 10.11648/j.mc.20190703.14
AMA Style
Bede Affoue Lucie, Kone Soleymane, N’Guessan Boka Robert, Yapo Kicho Denis, Ziao Nahosse. A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives. Mod Chem. 2019;7(3):65-72. doi: 10.11648/j.mc.20190703.14
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Download@article{10.11648/j.mc.20190703.14,
author = {Bede Affoue Lucie and Kone Soleymane and N’Guessan Boka Robert and Yapo Kicho Denis and Ziao Nahosse},
title = {A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives},
journal = {Modern Chemistry},
volume = {7},
number = {3},
pages = {65-72},
doi = {10.11648/j.mc.20190703.14},
url = {https://doi.org/10.11648/j.mc.20190703.14},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20190703.14},
abstract = {The 2-phenylbenzothiazole derivatives have antitumor activities. Work has shown that these derivatives have mesomeric forms. The electrophilic centers of these mesomers form adducts with the nucleophilic centers of deoxyribonucleic acid (DNA). These adducts destroy the tumor cells and prevent the proliferation of these. In this sense, the knowledge of electrophilic sites, nucleophiles and the capacity to protonate these derivatives is therefore useful if we want to know their future in the biological environment. Using DFT/B3LYP method associated with the bases 6-31G (d, p) and 6-31+G (d, p), this work aims at determining the preferential protonation site, the electrophilic and nucleophilic centers of six 2-phenylbenzothiazole. This study also analyzes the stability of these derivatives. Calculations are carried out in gas and aqueous phases. Results show that fluorinated derivatives are the most stable. 2-(4-aminophenyl) benzothiazoles are the most reactive. The atoms carbon C4, C5 and C6 of benzothiazole ring are the most electrophilic. Interactions of these derivatives with nucleophilic centers of deoxyribonucleic acid (DNA) will probably be at these atoms. Nitrogen sp2 (N1) of benzothiazole ring remains the most nucleophilic center and the preferential site of protonation in all the molecules studied. These results highlight the influence of the substituents on the basicity of the nitrogen sp2 (N1) and reactivity of the 2-phenylbenzothiazole derivatives studied.},
year = {2019}
}
TY - JOUR T1 - A Theoretical Study on the Stability, Reactivity and Protonic Affinity of 2-Phenylbenzothiazole Derivatives AU - Bede Affoue Lucie AU - Kone Soleymane AU - N’Guessan Boka Robert AU - Yapo Kicho Denis AU - Ziao Nahosse Y1 - 2019/09/29 PY - 2019 N1 - https://doi.org/10.11648/j.mc.20190703.14 DO - 10.11648/j.mc.20190703.14 T2 - Modern Chemistry JF - Modern Chemistry JO - Modern Chemistry SP - 65 EP - 72 PB - Science Publishing Group SN - 2329-180X UR - https://doi.org/10.11648/j.mc.20190703.14 AB - The 2-phenylbenzothiazole derivatives have antitumor activities. Work has shown that these derivatives have mesomeric forms. The electrophilic centers of these mesomers form adducts with the nucleophilic centers of deoxyribonucleic acid (DNA). These adducts destroy the tumor cells and prevent the proliferation of these. In this sense, the knowledge of electrophilic sites, nucleophiles and the capacity to protonate these derivatives is therefore useful if we want to know their future in the biological environment. Using DFT/B3LYP method associated with the bases 6-31G (d, p) and 6-31+G (d, p), this work aims at determining the preferential protonation site, the electrophilic and nucleophilic centers of six 2-phenylbenzothiazole. This study also analyzes the stability of these derivatives. Calculations are carried out in gas and aqueous phases. Results show that fluorinated derivatives are the most stable. 2-(4-aminophenyl) benzothiazoles are the most reactive. The atoms carbon C4, C5 and C6 of benzothiazole ring are the most electrophilic. Interactions of these derivatives with nucleophilic centers of deoxyribonucleic acid (DNA) will probably be at these atoms. Nitrogen sp2 (N1) of benzothiazole ring remains the most nucleophilic center and the preferential site of protonation in all the molecules studied. These results highlight the influence of the substituents on the basicity of the nitrogen sp2 (N1) and reactivity of the 2-phenylbenzothiazole derivatives studied. VL - 7 IS - 3 ER -
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