Syntheses, single crystal X-ray structure, Hirshfeld surface analyses, DFT computations and Monte Carlo simulations of New Eugenol derivatives bearing 1,2,3-triazole moiety

Taia A., El Ibrahimi B., Benhiba F., Ashfaq M., Tahir M. N., Essaber M., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1234, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1234
  • Publication Date: 2021
  • Doi Number: 10.1016/j.molstruc.2021.130189
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Hacettepe University Affiliated: Yes


A novel series of 1,2,3-triazole derivatives containing the eugenol ring (3 and 4) were synthesized in good yields (78 and 82%, respectively) by click chemistry method [Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC)]. We report here the cycloaddition reactions involving azides namely 1-azidoheptane (2a) and 1-azido-4-methylbenzene (2b), as well as 4-allyl-2-methoxy-1-(prop-2-yn-1-yloxy)benzene (1) as dipolarophiles. The structures of 3 and 4 were characterized by NMR spectroscopy and confirmed by a single crystal X-ray diffraction study. Predicted spectral data were also obtained using density functional theory (DFT) at the B3LYP/6-31G(d,p) level of theory. Also, the closest contacts between active atoms of the compounds studied were identified through Hirshfeld surface analyses. Based on the Monte Carlo simulation results, compound 4 can act as a good acidic corrosion inhibitor for iron. (C) 2021 Published by Elsevier B.V.