Lower rim thiacalixarenes derivatives incorporating multiple coordinating carbonyl groups: Synthesis, characterization, ion-responsive ability and DFT computational analysis

Aly Abdou, Omran A. Omran, Jabir H. Al-Fahemi, Rabab S. Jassas, Munirah M. Al-Rooqi, Essam M. Hussein, Ziad Moussa, Saleh A. Ahmed

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

Three novel tetra substituted p‑tert-butylthiacalix[4]arene derivatives (3, 4, and 5) with five coordinating carbonyl groups at the lower rims were synthesized. Accordingly, diethyl tetra-t‑butyl‑trihydroxy-tetrathia-tetrabenzenacyclooctaphanyl)oxy)malonate react with ethyl bromoacetate, phenacyl bromide and 2‑chloro-N-(p-tolyl)acetamide, to produce new p‑tert-butylthiacalix[4]arenes in of 60, 90, and 80% yields, respectively. The molecular structures of the products were verified using FT-IR, 1H NMR, and 13C NMR spectroscopy. Metal ions such as Na+, K+, Cs+, Hg2+, Cd2+, Pb2+, Ni2+, Co2+, Cu2+, and Ag+ are easily chelated by the new thiacalixarene derivatives using liquid-liquid extraction technique. These compounds surprisingly show high efficiency in liquid-liquid extraction of alkali, heavy, and transition metal ions. Uptake efficiencies of 71.00% (for Co(II)), 46.00% (for Cu(II), and 15.00% (for Hg(II)) were attained by thiacalixarene 3, 4, and 5. These derivatives were subjected to DFT-based computational analysis with the aim of increasing the efficiency with which thiacalixarene (as a nucleophilic) interacts with the metal ion (3, 4, and 5 in the role of electrophile).

Original languageEnglish
Article number136264
JournalJournal of Molecular Structure
Volume1293
DOIs
Publication statusPublished - Dec 5 2023

Keywords

  • DFT computational analysis
  • Liquid-liquid extraction
  • Metal ion detection
  • Molecular electrostatic potential (MEP)
  • Thiacalixarenes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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