Syntheses, spectroscopic characterization and metal ion binding properties of benzo-15-crown-5 derivatives and their sodium and nickel(II) complexes

Abstract

New benzo-15-crown-5 derivatives containing nitro, amine and imine groups were prepared. Nitro compound (1) was prepared after the reaction 4 0 ,5 0 -bis(bromethyl)benzo-15-crown-5 and o-nitrophenol in the presence of NaOH. After reduction process by using hydrazine hydrate and Pd/C amine compound (2) was formed. New crown ether imine compounds (3-5) were synthesized by the condensation of corresponding crown ether diamine (2) with salicylaldehyde derivatives. Sodium complexes of the crown compounds (1a-5a) form crystalline 1:1 (Na ? : ligand) complexes with sodium perchlorate. Nickel(II) complexes (3b-5b) with 1:1 (Ni 2? :ligand) stoichiometries were also been synthesized from the Schiff bases (3-5). The results indicated that the Schiff base ligands coordinated through the azomethine nitrogen and phenolic oxygen. The extraction ability of compounds (1, 3, 4 and 5) were also evaluated in chloroform by using several alkali and transition metal picrates such as

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

“…These results indicate that the electronic effect of the side arm attached to benzo crown ether alters the cation‐binding ability. The extraction trends of new p ‐substituted crown compounds ( 1–5 ) and previously worked o ‐substituted crown compounds were compared. p ‐Substituted crown compounds ( 1–5 ) showed higher extraction capabilities than o ‐substituted crown compounds for the studied metal cations (Na + , K + , Cr 3+ , Cu 2+ , Zn 2+ , and Pb 2+ ).…”

“…Ultravoilet–visible (UV–vis) spectra were recorded using a Unicam UV2‐100 series spectrophotometer (UK). Extraction studies were almost the same as those described in the previous paper (Note: Picric acid is explosive but also highly shock‐, heat‐, and friction sensitive. Do not allow picric acid and metal picrates to come in contact with skin, eyes, or respiratory tract at any time).…”

“…In a previous paper , we have prepared double‐armed benzo‐15‐crown‐5 derivatives. In this paper, 4′,5′‐bis(bromomethyl)benzo‐15‐crown‐5 and ortho ‐nitrophenol were used as starting materials.…”

Synthesis and characterization of transition metal complexes of a hexadentate N4O2 donor Schiff base ligand: X-ray crystal structures of the copper(II) and zinc(II) complexes and their antibacterial properties

“…Recently, we and others have reported the synthesis, characterization and antibacterial studies of some new Schiff base complexes [11][12][13][14][15][16]. The present work describes the synthesis and characterization of a new hexadentate N 4 O 2 donor Schiff base ligand L and some of its metal complexes, including spectroscopic and X-ray crystallographic studies.…”

“…The preparation of this green microcrystalline complex followed the same procedure described for (7) 36.457 (7) b (Å ) 10.920 (2) 10.965 (2) c (Å ) 16 …”