Issue 11, 2020

Synthesis and structural studies of copper(ii) complex with N2S2 based N-substituted pendant phosphonic acid arms

Abstract

The synthesis of a heteromacrocyclic bifunctional chelator with phosphonic acid pendent arms is presented along copper(II) complexation. Ligand N2S2-POH featuring N,N′-bis-substituted phosphonate pendent arms was isolated in respectable yields, characterized, and chelated to copper(II). Implementation of both Moedritzer–Irani and Kabachnik–Fields conditions using aza–thia macrocycle 1,8-dithia-4,11-diazacyclotetradecane afforded 1,8-dithia-4,11-diazacyclotetradecane-4,11-diyl-bis-(methylene)-bis-(phosphonic acid) (N2S2-POH). Kinetic NMR studies provided four acid dissociation constants with respect to hydronium ion concentration. Benesi–Hildebrand binding experiment provided a conditional formation constant of 2.8 × 104 M−1. Heteromacrocycle N2S2-POH readily formed an encapsulated copper(II) chelate at room temperature, which was examined through EPR analysis.

Graphical abstract: Synthesis and structural studies of copper(ii) complex with N2S2 based N-substituted pendant phosphonic acid arms

Supplementary files

Article information

Article type
Paper
Submitted
23 Dec 2019
Accepted
25 Feb 2020
First published
25 Feb 2020

Dalton Trans., 2020,49, 3545-3552

Author version available

Synthesis and structural studies of copper(II) complex with N2S2 based N-substituted pendant phosphonic acid arms

I. S. Taschner, E. Aubuchon, B. R. Schrage, C. J. Ziegler and A. van der Est, Dalton Trans., 2020, 49, 3545 DOI: 10.1039/C9DT04869C

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