Synthesis and Spectroscopic Characterization of New Double‐Armed Benzo‐15‐Crown‐5 Derivatives and Their Sodium Complexes

Abstract

Double‐armed crown ether aldehydes (1–3) were synthesized from the reaction of 2 equiv salicylaldehyde, 4‐hydroxy‐3‐methoxybenzaldehyde (vanillin), and 3‐hydroxy‐4‐methoxybenzaldehyde (iso‐vanillin) with 4′,5′‐bis(bromomethyl)benzo‐15‐crown‐5. New crown ethers imine compounds (4–9) were synthesized by the condensation of corresponding crown ether aldehydes (1–3) with 4‐amino‐1,2‐dihydro‐1,5‐dimethyl‐2‐phenyl‐3H‐pyrazole‐3‐one and 2‐furan‐2‐yl‐methylamine. Sodium complexes (1a–9a) of the crown compounds form crystalline 1:1 (Na+:ligand) stoichiometries and were also synthesized. The structures of the crown ether aldehydes (1–3), imine compounds (4–9), and complexes (1a–9a) were confirmed on the basis of elemental analyses, IR, 1H and 13C NMR, and mass spectrometry. © 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:100–109, 2013; View this article online at http://wileyonlinelibrary.com. DOI 10.1002/hc.21070

Double‐Armed Benzo‐15‐crown‐5 Ligands and Complexes and Single Crystal Structure Determination

“…The 1 H‐NMR spectra of the sodium complexes ( 1a–5a ) are approximately the same as in the corresponding ligands spectra, but, the 1 H‐NMR spectra provide compelling evidence for the ligands and their metal complexes ; because different multiplet peaks shapes were detected in crown ether protons (OCH 2 –CH 2 O) (between 3.5–4.5 ppm) of the ligands and each sodium complex . Although three multiplet peaks were observed for the ligands ( 1–5 ), four multiplet peaks were seen for the sodium complexes ( 1a–5a ) in crown ether proton peaks (OCH 2 –CH 2 O) region (Fig.…”

Synthesis, characterization, and metal-ion binding properties of a new macrobicyclic ligand with dioxadiazaoctathia donor atoms

“…The first synthesis of macrocyclic ligand was reported by Perdersen in 1967 . Since then, a very large number of macrocyclic ligands have been synthesized to understand their spectral, structural, electrochemical, and thermodynamic properties . In particular, complexation ability of macrocyclic compounds with various metal ions has received considerable attention in recent times.…”