Synthesis and theoretical study of the stability and reactivity of some 2-[(benzimidazolyl)methylthio]-4,5-diphenylimidazole derivatives using the density functional theory (DFT) method

Authors

  • COULIBALY Bamoro Department of Agro-Industrial Sciences and Technologies (AIST), UFR Agriculture, Halieutic Resources and Agro-Industry (AHRAI), University of San Pedro, San Pedro, Ivory Coast. https://orcid.org/0009-0008-1990-1788
  • DIOMANDE Sékou Department of Agro-Industrial Sciences and Technologies (AIST), UFR Agriculture, Halieutic Resources and Agro-Industry (AHRAI), University of San Pedro, San Pedro, Ivory Coast. https://orcid.org/0009-0000-9938-3723
  • SANGARE Kassoum Department of Agro-Industrial Sciences and Technologies (AIST), UFR Agriculture, Halieutic Resources and Agro-Industry (AHRAI), University of San Pedro, San Pedro, Ivory Coast. https://orcid.org/0009-0004-4987-1138
  • ABLE Anoh Valentin Department of Sciences of Structure and Matter (SSMT), Laboratory of Constitution and Reaction of Matter (LCRM), University of Félix Houphouët-Boigny, Abidjan, Ivory Coast. https://orcid.org/0009-0004-6959-9581
  • Aurélie Vallin Laboratory of Glycochemistry, Antimicrobials and Agroresources (LG2A), UMR 7378 CNRS, University of Picardie Jules Verne, Amiens, France. https://orcid.org/0009-0009-4985-8458
  • FANTE Bamba Department of Sciences of Structure and Matter (SSMT), Laboratory of Constitution and Reaction of Matter (LCRM), University of Félix Houphouët-Boigny, Abidjan, Ivory Coast

Abstract

The stability and reactivity of the five (5) 2-[(benzimidazolyl)methylthio]-4,5-diphenylimidazole derivatives were studied using density functional theory at the B3LYP/6-31+ G (d, p) level. Analysis of the molecular electrostatic potential (MEP) map and determination of the dual descriptor showed that nitrogen N13, sulfur S5 and carbons C19 and C21 are nucleophilic. They are therefore susceptible to electrophilic attack. The nitrogens N2, N3 and N14 are shared between electrophilic and nucleophilic sites. The study of the chemical reactivity of our compounds was carried out based on the analysis of molecular frontier orbitals (HOMO and LUMO), energy gap (ΔƐ), chemical hardness (η), electrophilicity (ω) and chemical softness (S). Compound 1 was found to be the most stable, the least reactive and electron-donating. This study also opens up a new way of synthesizing biologically active molecules by modulating the C19 carbon with inductive electroattractant groups.

Keywords: Benzimidazole, Imidazole, DFT, ESP, reactivity, stability.

Keywords:

Benzimidazole, Imidazole, DFT, ESP, reactivity, stability

DOI

https://doi.org/10.22270/jddt.v14i10.6816

Author Biographies

COULIBALY Bamoro, Department of Agro-Industrial Sciences and Technologies (AIST), UFR Agriculture, Halieutic Resources and Agro-Industry (AHRAI), University of San Pedro, San Pedro, Ivory Coast.

Department of Agro-Industrial Sciences and Technologies (AIST), UFR Agriculture, Halieutic Resources and Agro-Industry (AHRAI), University of San Pedro, San Pedro, Ivory Coast.

DIOMANDE Sékou, Department of Agro-Industrial Sciences and Technologies (AIST), UFR Agriculture, Halieutic Resources and Agro-Industry (AHRAI), University of San Pedro, San Pedro, Ivory Coast.

Department of Agro-Industrial Sciences and Technologies (AIST), UFR Agriculture, Halieutic Resources and Agro-Industry (AHRAI), University of San Pedro, San Pedro, Ivory Coast.

SANGARE Kassoum, Department of Agro-Industrial Sciences and Technologies (AIST), UFR Agriculture, Halieutic Resources and Agro-Industry (AHRAI), University of San Pedro, San Pedro, Ivory Coast.

Department of Agro-Industrial Sciences and Technologies (AIST), UFR Agriculture, Halieutic Resources and Agro-Industry (AHRAI), University of San Pedro, San Pedro, Ivory Coast.

ABLE Anoh Valentin, Department of Sciences of Structure and Matter (SSMT), Laboratory of Constitution and Reaction of Matter (LCRM), University of Félix Houphouët-Boigny, Abidjan, Ivory Coast.

Department of Sciences of Structure and Matter (SSMT), Laboratory of Constitution and Reaction of Matter (LCRM), University of Félix Houphouët-Boigny, Abidjan, Ivory Coast.

Aurélie Vallin, Laboratory of Glycochemistry, Antimicrobials and Agroresources (LG2A), UMR 7378 CNRS, University of Picardie Jules Verne, Amiens, France.

Laboratory of Glycochemistry, Antimicrobials and Agroresources (LG2A), UMR 7378 CNRS, University of Picardie Jules Verne, Amiens, France.

FANTE Bamba, Department of Sciences of Structure and Matter (SSMT), Laboratory of Constitution and Reaction of Matter (LCRM), University of Félix Houphouët-Boigny, Abidjan, Ivory Coast

Department of Sciences of Structure and Matter (SSMT), Laboratory of Constitution and Reaction of Matter (LCRM), University of Félix Houphouët-Boigny, Abidjan, Ivory Coast

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Published

15-10-2024
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How to Cite

1.
Bamoro C, Sékou D, Kassoum S, Anoh Valentin A, Vallin A, Bamba F. Synthesis and theoretical study of the stability and reactivity of some 2-[(benzimidazolyl)methylthio]-4,5-diphenylimidazole derivatives using the density functional theory (DFT) method. J. Drug Delivery Ther. [Internet]. 2024 Oct. 15 [cited 2025 Jan. 21];14(10):24-30. Available from: https://jddtonline.info/index.php/jddt/article/view/6816

How to Cite

1.
Bamoro C, Sékou D, Kassoum S, Anoh Valentin A, Vallin A, Bamba F. Synthesis and theoretical study of the stability and reactivity of some 2-[(benzimidazolyl)methylthio]-4,5-diphenylimidazole derivatives using the density functional theory (DFT) method. J. Drug Delivery Ther. [Internet]. 2024 Oct. 15 [cited 2025 Jan. 21];14(10):24-30. Available from: https://jddtonline.info/index.php/jddt/article/view/6816