| Peer-Reviewed

Theoretical Study of Reactivity and Stability of a Thiazoline Derivative Series by the Density Functional Theory Method

Received: 1 September 2022     Accepted: 16 September 2022     Published: 24 October 2022
Views:       Downloads:
Abstract

This reactivity and stability work was performed on six (6) Thiazoline derivatives using density functional theory at the B3LYP/6-31+ G (d, p) level. The aim was to determine the electrophilic and nucleophilic sites and the chemical behaviour of thiazolines. To do this, we calculated the fukui reactivity parameters (f+; f-), as well as the conceptual DFT reactivity parameters. The analysis of local descriptors and the molecular electrostatic potential map identified the nitrogen (N) atoms of the Thiazoline ring as the preferred electrophilic attack site (nucleophilic site) for the compound series. Moreover, the Natural Population Analysis (NPA) also corroborated this same information, that is to say the sulfur atoms (S) are electrophilic sites and the nitrogen atoms the nucleophilic sites of the compounds studied. Also, the sulfur atones that bind the linker were designated as the nucleophilic attack site (electrophilic site). The study of the boundary molecular orbitals, including energy gap (ΔE), electronegativity (χ), chemical hardness (η), and electrophilicity index (ω) allowed the chemical reactivity of Thiazoline derivatives to be described from the molecular properties. Thus, the Th3 molecule is the most stable, least reactive and hardest. Moreover, the Th3 compound is the one which gives the least electrons on all the studied molecules.

Published in American Journal of Applied Chemistry (Volume 10, Issue 5)
DOI 10.11648/j.ajac.20221005.16
Page(s) 156-163
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), 2022. Published by Science Publishing Group

Keywords

Local Reactivity, Global Reactivity, Thiazoline, DFT

References
[1] C. Walsh et E. M. Nolan, “Morphing peptide backbones into heterocycles,” Proceedings of the National Academy of Sciences, vol. 105, n° %115, p. 5655–5656, 2008.
[2] W. Wang, B. Zhao, C. Xu et W. Wu, “Synthesis and Antitumor Activity of the Thiazoline and Thiazine Multithioether,” International Journal of Organic Chemistry, vol. 2, pp. 117-120, 2012.
[3] A. Adams et N. De Kimpe, “Chemistry of 2-Acetyl-1-pyrroline, 6-Acetyl-1, 2, 3, 4-tetrahydropyridine, 2-Acetyl-2-thiazoline, and 5-Acetyl-2, 3-dihydro-4H-thiazine: Extraordinary Maillard Flavor Compounds,” Chemical Reviews, vol. 106, n° %16, p. 2006, 2299-2319.
[4] D. M. Du, S. F. Lu, T. Fang et J. X. Xu, “Asymmetric Henry Reaction Catalyzed by C2-SymmetrTridentate Bis(oxazoline) and Bis(thiazoline) Complexes: Metal-Controlled Reversal of Enantioselectivity,” Journal of Organic Chemistry, vol. 70, n° %19, pp. 3712-3715, 2005.
[5] Z. Jin, “Muscarine, Imidazole, Oxazole, and Thiazole Alkaloids,” Natural Product Reports, vol. 20, n° %16, pp. 584-605, 2003.
[6] M. Kurt, T. R. Sertbakan et M. Ozduran, “Spectrochim, An experimental and theoretical study of molecular structure and vibrational spectra of 3-and 4-pyridineboronic acid molecules by density functional theory calculations,” Acta Part A: Mol. Biomol. Spectrosc., vol. 70, n° %13, pp. 664-673, 2008.
[7] K. V. Bohoussou, A. Bénié, G.-R. M. Koné, N. Y. S. Diki, K. A. R. Kouassi et N. Ziao, “Contribution to Reactivity, Stability and Selectivity of Monodentated Free Phosphines,” Modern Chemistry, vol. 7, n° %12, pp. 38-44, 2019.
[8] T. I. Oprea, “Chemoinformatics in Drug Discovery,” Ed. WILEY-VCH Verlag., 2005.
[9] E. A. Rekka et P. N. Kourounakis, “Chemistry and Molecular Aspects of Drug Design and Action,” Ed. Taylor & Francis Group, 2008.
[10] C. Lee, W. Yang et R. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Physical Review Journals, vol. B37, p. 785, 1988.
[11] D. Becke, “Density-functional thermochemistry III. The role of exact exchange,” Journal of Chemical Physics, vol. 98, p. 5648, 1993.
[12] N. Tuo, G. Dembele, D. Soro, F. Konate, B. Konate, C. Kodjo et N. Ziao, “Theoretical Study of the Chemical Reactivity of a Series of 2, 3-Dihydro-1H-Perimidine,” International Research Journal of Pure & Applied Chemistry, vol. 23, n° %11, pp. 13-25, 2022.
[13] M. J. Frisch, G. W. Trucks, H. B. Schlegel et G. E. Scuseria, Gaussian, Inc Gaussian 09, Revision A. 02, Wallingford CT,, 2009.
[14] J. Kapp, M. Remko et P. v. R. Schleyer, “H2XO and (CH3)2XO Compounds (X= C, Si, Ge, Sn, Pb): Double bonds vs carbene-like structures can the metal compounds exist at all?”, Journal of the American Chemical Society, vol. 118, pp. 5745-5751, 1996.
[15] B. G. Johnson, P. M. Gill et J. A. Pople, “The performance of a family of density functional methods”, The Journal of Chemical Physics, vol. 98, pp. 5612-5626, 1993.
[16] R. G. Parr et W. Yang, “Density-functional theory of the electronic structure of molecules,” Annual Review Physical Chemistry, vol. 46, pp. 701-728, 1995.
[17] W. K. Coulibaly, J. N’dri, M. G.-R. Koné, C. D. Dago, C. N. Ambeu, J.-P. Bazureau et N. Ziao, “Studies of the Chemical Reactivity of a Series of Rhodanine Derivatives by Approaches to Quantum Chemistry,” Computational Molecular Bioscience, vol. 9, pp. 49-62, 2019.
[18] T. Koopmans, “Úber die Zuordnung von Wellenfunktiomen und Eigenwerten zu den einzelnen Elektronen eines Atoms,” Physica, vol. 1, pp. 104-113, 1934.
[19] S. Dheivamalar, L. Sugi et K. Ambigai, “Density Functional Theory Study of Exohedral Carbon Atoms Effect on Electrophilicity of Nicotine : Comparative Analysis,” p. 17–31, January 2016.
[20] P. W. Ayers et R. G. Parr, “Variational Principles for Describing Chemical Reactions: The Fukui Function and Chemical Hardness Revisited,” J. Am. Chem. Soc., vol. 122, n° %19, p. 2010–2018, Mars 2000.
[21] K. Fukui, T. Yonezawa et H. Shingu, “A Molecular Orbital Theory of Reactivity in Aromatic Hydrocarbons,” J. Chem. Phys., vol. 20, n° %14, p. 722–725, April 1952.
[22] C. Morell, A. Grand et A. Toro-Labbé, “Theoretical support for using the Δf(r) descriptor”, Chem. Phys. Lett, vol. 425, n° %14–6, p. 342–346, Juillet 2006.
[23] J. S. N’dri, M.-R. Koné, C. G. Kodjo, A. L. C. kablan, S. T. Affi, L. Ouattara et N. Ziao, “Theoretical Study of the Chemical Reactivity of Five Schiff Bases Derived From Dapsone by the DFT Method,” Chemical Science International Journal, vol. 22, n° %14, pp. 1-11, 2018.
[24] F. L. Hirshfeld, “Bonded-atom fragments for describing molecular charge densities,” Theor. Chim. Acta, vol. 44, n° %12, p. 129–138, 1977.
[25] F. J. Luque, J. M. López et M. Orozco, “Perspective on Electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects.” Theoretical Chemistry Accounts, vol. 103, n° %13-4, p. 343–345, 2000.
[26] S. Sebastian et N. Sundaraganesan, “The spectroscopic (FT-IR, FT-IR gas phase, FT Raman and UV) and NBO analysis of 4-Hydroxypiperidine by density functional method,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 75, n° %13, p. 941–952, 2010.
Cite This Article
  • APA Style

    Nanou Tieba Tuo, Bafetigue Ouattara, Mamadou Guy Richard Kone, Georges Stephane Dembele, Doh Soro, et al. (2022). Theoretical Study of Reactivity and Stability of a Thiazoline Derivative Series by the Density Functional Theory Method. American Journal of Applied Chemistry, 10(5), 156-163. https://doi.org/10.11648/j.ajac.20221005.16

    Copy | Download

    ACS Style

    Nanou Tieba Tuo; Bafetigue Ouattara; Mamadou Guy Richard Kone; Georges Stephane Dembele; Doh Soro, et al. Theoretical Study of Reactivity and Stability of a Thiazoline Derivative Series by the Density Functional Theory Method. Am. J. Appl. Chem. 2022, 10(5), 156-163. doi: 10.11648/j.ajac.20221005.16

    Copy | Download

    AMA Style

    Nanou Tieba Tuo, Bafetigue Ouattara, Mamadou Guy Richard Kone, Georges Stephane Dembele, Doh Soro, et al. Theoretical Study of Reactivity and Stability of a Thiazoline Derivative Series by the Density Functional Theory Method. Am J Appl Chem. 2022;10(5):156-163. doi: 10.11648/j.ajac.20221005.16

    Copy | Download

  • @article{10.11648/j.ajac.20221005.16,
      author = {Nanou Tieba Tuo and Bafetigue Ouattara and Mamadou Guy Richard Kone and Georges Stephane Dembele and Doh Soro and Fandia Konate and Bibata Konate and Nahosse Ziao},
      title = {Theoretical Study of Reactivity and Stability of a Thiazoline Derivative Series by the Density Functional Theory Method},
      journal = {American Journal of Applied Chemistry},
      volume = {10},
      number = {5},
      pages = {156-163},
      doi = {10.11648/j.ajac.20221005.16},
      url = {https://doi.org/10.11648/j.ajac.20221005.16},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajac.20221005.16},
      abstract = {This reactivity and stability work was performed on six (6) Thiazoline derivatives using density functional theory at the B3LYP/6-31+ G (d, p) level. The aim was to determine the electrophilic and nucleophilic sites and the chemical behaviour of thiazolines. To do this, we calculated the fukui reactivity parameters (f+; f-), as well as the conceptual DFT reactivity parameters. The analysis of local descriptors and the molecular electrostatic potential map identified the nitrogen (N) atoms of the Thiazoline ring as the preferred electrophilic attack site (nucleophilic site) for the compound series. Moreover, the Natural Population Analysis (NPA) also corroborated this same information, that is to say the sulfur atoms (S) are electrophilic sites and the nitrogen atoms the nucleophilic sites of the compounds studied. Also, the sulfur atones that bind the linker were designated as the nucleophilic attack site (electrophilic site). The study of the boundary molecular orbitals, including energy gap (ΔE), electronegativity (χ), chemical hardness (η), and electrophilicity index (ω) allowed the chemical reactivity of Thiazoline derivatives to be described from the molecular properties. Thus, the Th3 molecule is the most stable, least reactive and hardest. Moreover, the Th3 compound is the one which gives the least electrons on all the studied molecules.},
     year = {2022}
    }
    

    Copy | Download

  • TY  - JOUR
    T1  - Theoretical Study of Reactivity and Stability of a Thiazoline Derivative Series by the Density Functional Theory Method
    AU  - Nanou Tieba Tuo
    AU  - Bafetigue Ouattara
    AU  - Mamadou Guy Richard Kone
    AU  - Georges Stephane Dembele
    AU  - Doh Soro
    AU  - Fandia Konate
    AU  - Bibata Konate
    AU  - Nahosse Ziao
    Y1  - 2022/10/24
    PY  - 2022
    N1  - https://doi.org/10.11648/j.ajac.20221005.16
    DO  - 10.11648/j.ajac.20221005.16
    T2  - American Journal of Applied Chemistry
    JF  - American Journal of Applied Chemistry
    JO  - American Journal of Applied Chemistry
    SP  - 156
    EP  - 163
    PB  - Science Publishing Group
    SN  - 2330-8745
    UR  - https://doi.org/10.11648/j.ajac.20221005.16
    AB  - This reactivity and stability work was performed on six (6) Thiazoline derivatives using density functional theory at the B3LYP/6-31+ G (d, p) level. The aim was to determine the electrophilic and nucleophilic sites and the chemical behaviour of thiazolines. To do this, we calculated the fukui reactivity parameters (f+; f-), as well as the conceptual DFT reactivity parameters. The analysis of local descriptors and the molecular electrostatic potential map identified the nitrogen (N) atoms of the Thiazoline ring as the preferred electrophilic attack site (nucleophilic site) for the compound series. Moreover, the Natural Population Analysis (NPA) also corroborated this same information, that is to say the sulfur atoms (S) are electrophilic sites and the nitrogen atoms the nucleophilic sites of the compounds studied. Also, the sulfur atones that bind the linker were designated as the nucleophilic attack site (electrophilic site). The study of the boundary molecular orbitals, including energy gap (ΔE), electronegativity (χ), chemical hardness (η), and electrophilicity index (ω) allowed the chemical reactivity of Thiazoline derivatives to be described from the molecular properties. Thus, the Th3 molecule is the most stable, least reactive and hardest. Moreover, the Th3 compound is the one which gives the least electrons on all the studied molecules.
    VL  - 10
    IS  - 5
    ER  - 

    Copy | Download

Author Information
  • Laboratory of Thermodynamics and Physico-Chemistry of the Environment, Université Nangui Abrogoua, Abidjan, Ivory Coast

  • Laboratory of Fundamental and Applied Physics, Université Nangui Abrogoua, Abidjan, Ivory Coast

  • Laboratory of Thermodynamics and Physico-Chemistry of the Environment, Université Nangui Abrogoua, Abidjan, Ivory Coast

  • Laboratory of Thermodynamics and Physico-Chemistry of the Environment, Université Nangui Abrogoua, Abidjan, Ivory Coast

  • Laboratory of Thermodynamics and Physico-Chemistry of the Environment, Université Nangui Abrogoua, Abidjan, Ivory Coast

  • Laboratory of Thermodynamics and Physico-Chemistry of the Environment, Université Nangui Abrogoua, Abidjan, Ivory Coast

  • Laboratory of Thermodynamics and Physico-Chemistry of the Environment, Université Nangui Abrogoua, Abidjan, Ivory Coast

  • Laboratory of Thermodynamics and Physico-Chemistry of the Environment, Université Nangui Abrogoua, Abidjan, Ivory Coast

  • Sections