Chemical Review and Letters

Synthesis and characterization of some novel lariat-type ligands as [ONS] donors of diamide crown compounds

Document Type : Research Article

Authors

Hassan Mazaheri Moghaddam
Samad Bavili Tabrizi
Elnaz Ghasemi

Department of Organic Chemistry, Faculty of Basic Sciences, Tabriz Branch, Islamic Azad University, Tabriz, Iran

10.22034/crl.2025.531929.1655
Abstract
Lariat-type ligands are a specialized class of macrocyclic ligands distinguished by the presence of one or more pendant arms or tail-like extensions attached to the macrocyclic core. These pendant arms typically contain donor atoms such as nitrogen, oxygen, or sulfur, which participate in metal coordination. The unique structural features of lariat-type ligands enable them to modulate the coordination environment and binding affinity toward metal ions. This study primarily focuses on the synthesis of novel lariat-type ligands that function as [ONS] donors for diamide crown compounds. The experimental procedure involved conversion of 2,4-dimethylphenol (2,4-DMP) into a bisphenol compound. Transformation of the bisphenol into a methyl diester derivative through reaction with methyl chloroacetate. Reaction of the methyl diester with a suitable diamine, triethylenetetramine, to produce the corresponding diamide macrocycle. Modification of the diamide macrocycle to obtain the lariat structure by reaction with various monofunctional agents, such as ditosylate, 4-chlorophenol, hexanoyl chloride, and formaldehyde. Finally, The structures of all synthesized compounds were thoroughly characterized and confirmed using a combination of spectroscopic techniques, including 1HNMR, 13CNMR, MS(mass spectrometry), and FT-IR spectroscopy. The reaction efficiency of lariat 4 and lariat 5 were 55% and 96% respectively. Also, the melting point of lariat 4 and lariat 5 171-174 °C and 153-155 °C respectively.

Graphical Abstract

Synthesis and characterization of some novel lariat-type ligands as [ONS] donors of diamide crown compounds

Keywords

Macrocycle
Lariat
Diamide crown compound
1HNMR
13CNMR
MS
FT-IR

Subjects

Chemical Review and Letters
Volume 8, Issue 5 - Serial Number 5
September and October 2025
Pages 1105-1110

  • Receive Date 13 July 2025
  • Revise Date 10 September 2025
  • Accept Date 13 September 2025

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