Cu(I)-<i>N</i>-heterocyclic carbene complexes bearing a naphthyl substituent: synthesis, characterization, and antimicrobial activities


Tokatli A., Demir B., Kiliç N., Kurt Kızıldoğan A., Otur Ç., Kilinçarslan R., ...Daha Fazla

JOURNAL OF COORDINATION CHEMISTRY, cilt.76, sa.13-15, ss.1745-1762, 2023 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 76 Sayı: 13-15
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1080/00958972.2023.2255361
  • Dergi Adı: JOURNAL OF COORDINATION CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Metadex
  • Sayfa Sayıları: ss.1745-1762
  • Anahtar Kelimeler: antimicrobial activity, biological activity, copper(I)–NHC, N-Heterocyclic carbene (NHC), naphthyl
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

A series of 1-(alkyl)-3-(1-naphthyl)imidazolinium bromides (2a-d) as N-heterocyclic carbene (NHC) precursors were synthesized from 3-(1-naphthyl)-1H-imidazolinium chloride (1). By reacting these NHC precursors with fresh CuCl, Cu(I)-NHC complexes (3a-d) were synthesized. The structures of the compounds were elucidated using H-1, C-13-NMR, FT-IR, ESI-MS, X-ray diffraction, scanning electron microscopy with energy-dispersive X-ray spectroscopy analysis, and elemental analysis techniques. The thermal properties of selected complexes were determined. Salts (1, 2a-d) and Cu(I)-NHC complexes (3a-d) were investigated against test microorganisms to determine their antimicrobial potency. The imidazolinium salts 2b and 2d displayed remarkable antibacterial efficacy, particularly against gram-positive bacteria; however, the corresponding Cu(I)-NHC derivatives (3a-d) did not exhibit a similar level of potency probably due to limited solubility. Overall, it can be concluded that incorporation of N-substituent species with O-heteroatoms, instead of benzyl, allyl, or hexyl groups on NHC, can enhance the activity against microbial derivatives.